1-Hydroxybenzotriazole → N-[1-(2-Benzyloxy-ethyl)-2-oxo-5-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-hydroxy-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 2219029Notes

Reaction equation

HRID 2219029 reaction equation
Cl.[NH2:2][CH:3]1[C:9](=[O:10])[N:8]([CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=2[N:5]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:4]1.[OH:30][C:31]([CH3:46])([C:35]([NH:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])=[O:36])[C:32](O)=[O:33].ON1C2C=CC=CC=2N=N1>>[CH2:14]([O:13][CH2:12][CH2:11][N:8]1[C:9](=[O:10])[CH:3]([NH:2][C:32](=[O:33])[C:31]([OH:30])([CH3:46])[C:35]([NH:37][CH2:38][C:39]([F:44])([F:45])[C:40]([F:41])([F:43])[F:42])=[O:36])[CH2:4][N:5]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]1=2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 21091408HCID 21091408, compoundHCID 692711803-Amino-1-(2-benzyloxy-ethyl)-5-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride

Product 1

HCID 59718690N-[1-(2-Benzyloxy-ethyl)-2-oxo-5-(2,2,2-trifluoro-ethyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-hydroxy-2-methyl-N'-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Procedure

In an analogous manner to that described in Example 1e), the condensation of 3-amino-1-(2-benzyloxy-ethyl)-5-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one hydrochloride and (RS)-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid with 1-hydroxy-benzotriazole and N-(3-dimethylaminpropyl)-N′-ethyl-carbodiimide hydrochloride as the condensating agents yielded a mixture of the four epimeric title compounds as a white foam; MS (m/e): 641 (M+H)+.

Workup

  1. customyielded
  2. additiona mixture of the four epimeric title compounds as a white foam

Sources & evidence

ORD record
ord-a9db61c261ef472a90aa8df40c8d833f
Source dataset
uspto-grants-2008_08
Patent number
US07414049B2

Reaction notes

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