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34649-22-4

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Basic Information
CAS No.: 34649-22-4
Name: oroidin
Article Data: 12
Molecular Structure:
Molecular Structure of 34649-22-4 (oroidin)
Formula: C11H11 Br2 N5 O
Molecular Weight: 389.049
Synonyms: 1H-Pyrrole-2-carboxamide,N-[3-(2-amino-1H-imidazol-4-yl)-2-propenyl]-4,5-dibromo-, (E)-; Oroidin;Oroidine
Density: 1.948g/cm3
Boiling Point: °Cat760mmHg
Flash Point: °C
PSA: 100.32000
LogP: 2.60920
Related products
Synthetic route
917919-56-3

tert-butyl (E)-[4-(3-(4,5-dibromo-1H-pyrrole-2-carboxamido)prop-1-enyl)-1H-imidazol-2-yl]carbamate

34649-22-4

oroidin

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃; for 1h; Inert atmosphere;98%
With hydrogenchloride In ethanol at 20℃; for 1h;92%
269064-68-8

(Z)-oroidin

34649-22-4

oroidin

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 50℃; for 2h;71%
1443034-58-9

(E)-4,5-dibromo-N-(3-(imidazo[1,2-a]pyrimidin-2-yl)allyl)-1H-pyrrole-2-carboxamide

34649-22-4

oroidin

Conditions
ConditionsYield
With hydrazine hydrate at 20℃; for 0.5h;65%

4,5-Dibromo-1H-pyrrole-2-carboxylic acid [3-((4R,5R)-2-amino-4,5-dimethoxy-4,5-dihydro-1H-imidazol-4-yl)-propyl]-amide; hydrobromide

A

34649-22-4

oroidin

B

4,5-Dibromo-1H-pyrrole-2-carboxylic acid [3-(2-amino-5-oxo-4,5-dihydro-1H-imidazol-4-yl)-propyl]-amide

Conditions
ConditionsYield
In methanol; xylene at 135℃; for 2h;A 48%
B 30%
34649-21-3

4,5-dibromo-1H-pyrrole-2-carboxylic acid

(E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine

34649-22-4

oroidin

Conditions
ConditionsYield
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Inert atmosphere;25%
Stage #1: 4,5-dibromo-1H-pyrrole-2-carboxylic acid With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: (E)-4-(3-aminoprop-1-en-1-yl)-1H-imidazol-2-amine In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;		25%
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 6h; regioselective reaction;

4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-azido-1H-imidazol-4-yl)-allyl]-amide

34649-22-4

oroidin

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In methanol at 20℃; for 3h;
917919-54-1

tert-butyl (E)-2-(tert-butoxycarbonylamino)-4-[3-(1,3-dioxoisoindolin-2-yl)prop-1-enyl]-1H-imidazol-1-carboxylate

34649-22-4

oroidin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / H2NNH2 / ethanol / 2 h / 50 °C
2: 79 percent / Na2CO3 / dimethylformamide / 20 °C
3: 92 percent / aq. HCl / ethanol / 1 h / 20 °C
View Scheme
917919-55-2

tert-butyl (E)-[4-(3-aminoprop-1-enyl)-1H-imidazol-2-yl]carbamate

34649-22-4

oroidin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / Na2CO3 / dimethylformamide / 20 °C
2: 92 percent / aq. HCl / ethanol / 1 h / 20 °C
View Scheme
50371-52-3

4,5-dibromopyrrol-2-yl trichloromethyl ketone

34649-22-4

oroidin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 79 percent / Na2CO3 / dimethylformamide / 20 °C
2: 92 percent / aq. HCl / ethanol / 1 h / 20 °C
View Scheme
110-86-1

pyridine

copper-powder

copper-powder

34649-22-4

oroidin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 20 percent / NaBH4 / tetrahydrofuran / 1.75 h / -78 °C
2: 42 percent / bromine / dimethylformamide; acetonitrile / 1 h / 20 °C
3: 47 percent / triethylamine; hydroxylamine hydrochloride / ethanol / 1 h / Heating
4: 71 percent / trifluoroacetic acid / CH2Cl2 / 2 h / 50 °C
View Scheme
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    34649-22-4

    oroidin

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