Phenylethanolamine → 10-[(4-Chlorophenoxy)acetyl]-N-(2-hydroxy-2-phenylethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 639275Notes

Reaction equation

HRID 639275 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19](=[O:29])[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[NH2:32][CH2:33][CH:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[OH:35]>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:32][CH2:33][CH:34]([OH:35])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:29])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 1000PhenylethanolamineHCID 160392192,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 1603929310-[(4-Chlorophenoxy)acetyl]-N-(2-hydroxy-2-phenylethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

Procedure

The title compound was synthesized from 2,2,2-trichloro-1-{10-[(4-chlorophenoxy)acetyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 67 (0.3 mmol) and 2-amino-1-phenylethanol (2.2 eq.) in the manner of Example 68, m.p. 157-158° C. MS [(−)ESI, m/z]: 514.3 [M−H]−

Sources & evidence

ORD record
ord-6d14ddffd6034f21aa56a655a82fcd88
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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