(3S,4S)-4-Aminopyrrolidin-3-ol dihydrochloride → 4-((3 S,4S)-3-amino-4-hydroxypyrrolidin-1-yl)-3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)benzamide

HRID 525752Notes

Reaction equation

HRID 525752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1F)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([Cl:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].Cl.Cl.[NH2:25][C@H:26]1[CH2:30][NH:29][CH2:28][C@@H:27]1[OH:31]>>[NH2:25][C@@H:26]1[C@@H:27]([OH:31])[CH2:28][N:29]([C:21]2[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([Cl:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:3][C:2]=2[Br:1])[CH2:30]1

Participants

3

Reactant 2

HCID 69959682(3S,4S)-4-Aminopyrrolidin-3-ol dihydrochlorideHCID 867026223-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-fluorobenzamide

Product 1

HCID 899064294-((3 S,4S)-3-amino-4-hydroxypyrrolidin-1-yl)-3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using 3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-4-fluorobenzamide (Stage 76.2) and (3S,4S)-4-aminopyrrolidin-3-ol dihydrochloride (Stage 76.3) to give the title product as a beige solid. HPLC (Condition 7) tR=6.08 min, UPLC-MS (Condition 3) tR=0.82 min, m/z=476.1/478.1 [M+H]+.

Workup

  1. customThe title compound was prepared in an analogous fashion to

Sources & evidence

ORD record
ord-76883fd283424d9aaf649e1a40c9e39f
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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