Triethylamine → N-(1-Ethyl-1H-benzimidazol-2-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide

HRID 1521755Notes

Reaction equation

HRID 1521755 reaction equation
[O:1]=[C:2]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:41]([N:43]1[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[N:45]=[C:44]1[NH2:52])[CH3:42].C(N(CC)CC)C>CN(C=O)C.O>[CH2:41]([N:43]1[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[N:45]=[C:44]1[NH:52][C:16]([C:13]1[CH:14]=[CH:15][C:10]2[N:9]=[C:8]3[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]3[C:11]=2[CH:12]=1)=[O:18])[CH3:42]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5951931-ethyl-1H-1,3-benzodiazol-2-amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 672364761-Oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid2×

Product 1

HCID 67240109N-(1-Ethyl-1H-benzimidazol-2-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamideYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid (Intermediate B, 103 mg, 0.42 mmol) and TBTU (149 mg, 0.46 mmol) in DMF (2 mL) is stirred for 10 min. 1-Ethyl-1H-benzimidazol-2-amine (68 mg, 0.42 mmol) and triethylamine (43 mg, 0.42 mmol) are added and the reaction is stirred at room temperature for 16 h. The reaction mixture is diluted with H2O. A yellow solid is formed that is filtered and washed with EtOAc and a small amount of methanol to afford the title compound (85 mg, 51%).

Workup

  1. customA yellow solid is formed
  2. filtrationthat is filtered
  3. washwashed with EtOAc

Sources & evidence

ORD record
ord-f22255ab9ffe4e8895e84ecc74709e94
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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