(2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide

Base Information

• Chemical Name: (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide
• CAS No.: 479232-57-0
• Molecular Formula: C₃₂H₄₀N₈O₂S
• Molecular Weight: 600.788
• Mol file: 479232-57-0.mol

Synonyms:

Chemical Property of (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide

Chemical Property:

Purity/Quality:

≥97% by HPLC ^*data from raw suppliers

TC OT 39 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: TC OT 39 is a non-peptide oxytocin agonist.

Technology Process of (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide

There total 17 articles about (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate (31037-02-2) → (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide (479232-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 62 percent / NaH / tetrahydrofuran

2: 92 percent / H₂ / Pd/C / methanol

3: 40 percent / dimethylsulfoxide / 2.5 h / 75 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran

5: Et₃N / CH₂Cl₂

6: 64 percent / NaBH₄; CoCl₂*6H₂O / methanol

7: i-PrNEt₂ / dimethylformamide

With sodium tetrahydroborate; lithium aluminium tetrahydride; N,N-diethyl-N-isopropylamine; hydrogen; sodium hydride; triethylamine; cobalt(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.04.107

Reference yield:

ortho-nitrofluorobenzene (1493-27-2,127723-77-7) → (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide (479232-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 62 percent / NaH / tetrahydrofuran

2: 92 percent / H₂ / Pd/C / methanol

3: 40 percent / dimethylsulfoxide / 2.5 h / 75 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran

5: Et₃N / CH₂Cl₂

6: 64 percent / NaBH₄; CoCl₂*6H₂O / methanol

7: i-PrNEt₂ / dimethylformamide

With sodium tetrahydroborate; lithium aluminium tetrahydride; N,N-diethyl-N-isopropylamine; hydrogen; sodium hydride; triethylamine; cobalt(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.04.107

Reference yield:

1,1'-carbonyldiimidazole (530-62-1) + (S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione (479234-57-6) + (4-(aminomethyl)-3-methylphenyl)(1-methyl-3a,4,10,10a-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methanone (479234-64-5) → (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide (479232-57-0)

Guidance literature:

With N,N-diethyl-N-isopropylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.04.107

upstream raw materials:

1,1'-carbonyldiimidazole

(S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione

(4-(aminomethyl)-3-methylphenyl)(1-methyl-3a,4,10,10a-tetrahydrobenzo[b]pyrazolo[3,4-e][1,4]diazepin-5(1H)-yl)methanone

ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate