Dichloromethane → HCID 71008507, compound

HRID 1887481Notes

Reaction equation

HRID 1887481 reaction equation
Cl.[F:2][C:3]([F:22])([F:21])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]3[CH2:17][NH:18][CH2:19][CH:13]3[C:12]2=[O:20])=[CH:7][CH:6]=1.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(CC)CC.C(Cl)Cl>C(Cl)Cl.CO>[C:23]1([CH2:29][C:30]([CH:17]2[CH:14]3[CH:13]([C:12](=[O:20])[N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][C:3]([F:2])([F:21])[F:22])=[CH:6][CH:7]=4)[CH2:16][CH2:15]3)[CH2:19][NH:18]2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 131730790HCID 131730790, compound

Product 1

HCID 71008507HCID 71008507, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

5-(4-Trifluoromethoxy-phenyl)-octahydro-pyrrolo[3,4-c]pyridin-4-one, hydrochloride (80 mg, 0.24 mmol), 2-phenylacetyl chloride (74 mg, 0.48 mmol) and Et3N (0.12 g, 1.2 mmol) were added to DCM (10 mL), and the mixture was stirred for 12 h at ambient temperature. The product (45 mg, 46%) was obtained by prep-TLC (eluting with DCM/MeOH=25/1). 1H NMR (300 MHz, CDCl3): δ 7.34-7.23 (m, 9H), 3.90-3.54 (m, 7H), 3.23-3.20 (m, 2H), 2.78-2.75 (m, 1H), 2.07-2.02 (m, 1H), 1.83 (bs, 1H); LC-MS: [M+1]+ 418.7.

Sources & evidence

ORD record
ord-5bd17df98dd74bb8aa76aec4e98975b7
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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