HCID 86705063, compound → HCID 70561537, compound

HRID 1427309Notes

Reaction equation

HRID 1427309 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9](=[N:11]O)[CH3:10])=[CH:4][CH:3]=1>CO.[Ni]>[NH2:11][CH:9]([C:8]([N:15]1[C:23]2[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:13][CH3:14])[CH3:10]

Participants

4

Reactant 1

HCID 86705063HCID 86705063, compound

Product 1

HCID 70561537HCID 70561537, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from Step A (68 mg, 0.162 mmol) and Raney-Ni (1 mg) in MeOH (10 mL) was purged air three times and then backfilled with H2. The mixture was stirred at ambient temperature overnight. The suspension was filtered off and the filtrate was concentrated to afford the title compound as a colorless solid. LC/MS m/z=406.0 [M+H]+. Compound 176 was obtained by the below chiral separation conditions:

Workup

  1. customwas purged air three times
  2. filtrationThe suspension was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e8e446aa4e25481e9ee799927c7e97c1
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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