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1256387-74-2

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Basic Information
CAS No.: 1256387-74-2
Name: 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-
Article Data: 9
Molecular Structure:
Molecular Structure of 1256387-74-2 (2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)-)
Formula: N/A
Molecular Weight: 392.296
Synonyms: (1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Density: 1.455±0.06 g/cm3(Predicted)
Boiling Point: 554.3±30.0 °C(Predicted)
Related products
Synthetic route

C18H24BrN3O3

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With acetic acid In tert-butyl methyl ether at 70℃; Reagent/catalyst; Solvent; Temperature;96.8%
With acetic acid In acetonitrile at 80℃; for 12h; Solvent;87%
1575-37-7

4-Bromo-benzene-1,2-diamine

(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: 4-Bromo-benzene-1,2-diamine; (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide at 10 - 20℃; for 20h; Cooling with ice;
Stage #2: With acetic acid In tert-butyl methyl ether at 55℃; for 18h;		94%
Stage #1: 4-Bromo-benzene-1,2-diamine; (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: In ethanol at 115℃; for 48h;		1.59 g
1256387-73-1

(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With ethanol at 130 - 170℃; for 72h; Sealed tube;72%
In ethanol at 130 - 170℃; Sealed tube;72%
24424-99-5

di-tert-butyl dicarbonate

1256387-73-1

(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Stage #1: 3-(2-amino-4-bromo-phenylcarbamoyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester In ethanol at 130 - 170℃; Sealed tube;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃;		72%
1256387-73-1

C18H24BrN3O3

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
With acetic acid at 50 - 60℃; for 3h;

(1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: ethanol / 130 - 170 °C / Sealed tube
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 130 - 170 °C / Sealed tube
View Scheme
Multi-step reaction with 3 steps
1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate; pyrographite / toluene; ethanol / 5 h / 60 - 65 °C
3: acetic acid / acetonitrile / 12 h / 80 °C
View Scheme
Multi-step reaction with 3 steps
1: pivaloyl chloride / -10 - -5 °C
2: pyridinium hydrobromide perbromide / N,N-dimethyl-formamide / 0 °C
3: acetic acid / tert-butyl methyl ether / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 72 h / 130 - 170 °C / Sealed tube
View Scheme
1575-37-7

4-Bromo-benzene-1,2-diamine

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: ethanol / 130 - 170 °C / Sealed tube
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
2: ethanol / 72 h / 130 - 170 °C / Sealed tube
View Scheme

(1R,3S,4S)-methyl 2-((R)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: palladium on carbon; hydrogen / ethanol; methanol / 15 h / 30 - 35 °C / 5171.62 Torr
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C
3: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
4: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
5: ethanol / 130 - 170 °C / Sealed tube
View Scheme

(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid methyl ester

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C
2: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
3: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
4: ethanol / 130 - 170 °C / Sealed tube
View Scheme
1181573-36-3

(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester

1256387-74-2

(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h
2: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C
3: ethanol / 130 - 170 °C / Sealed tube
View Scheme
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