Methanol → HCID 178522003, compound

HRID 1748353Notes

Reaction equation

HRID 1748353 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]5[N:26]=[CH:27][N:28](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:29]=5)[CH:20]=4)=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.CO.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[CH:29]=[C:25]([C:21]2[CH:20]=[C:19]([NH:18][C:16]([C:13]3[CH:12]=[CH:11][C:10]4[CH:9]=[C:8]5[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]5[C:15]=4[CH:14]=3)=[O:17])[CH:24]=[CH:23][CH:22]=2)[N:26]=[CH:27]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 683235541-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

Product 1

HCID 178522003HCID 178522003, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide from the preceding step in CH2Cl2 (1.5 mL) and methanol (1.5 mL) is added TFA (1.0 mL). The reaction is stirred for 16 h at room temperature. The solvents are evaporated and the crude material is purified by preparative HPLC using 10-80% acetonitrile/water with 0.1% TFA to afford the title compound (43 mg, 35% for 2 steps). LCMS (ESMS): m/z 386.20 (M+H+).

Workup

  1. customThe solvents are evaporated
  2. customthe crude material is purified by preparative HPLC

Sources & evidence

ORD record
ord-09ae61eebaa64b7c9b251772df8a8683
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…