Chloroacetyl chloride → HCID 57686028, compound

HRID 1038112Notes

Reaction equation

HRID 1038112 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=3)=[CH:10][C:9]=2[F:20])=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>ClCCl.CN(C)C=O>[Cl:28][CH2:29][C:30]([N:17]1[CH2:16][CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=3)=[C:9]([F:20])[CH:10]=2)[CH2:19][CH2:18]1)=[O:31]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 57686277HCID 57686277, compound

Product 1

HCID 57686028HCID 57686028, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5-Fluoro-2-[2-fluoro-4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-pyrimidine (22AB) (1.94 g, 7.1 mmol, 1 equiv) was dissolved in a (3v:1v) mixture of dichloromethane (30 mL) and N,N-dimethyl formamide (10 mL) and triethylamine (862 mg, 1.19 mL, 8.52 mmol, 1.2 equiv) was added, followed by slow addition of chloroacetyl chloride (962 mg, 678 uL, 8.52 mmol, 1.2 equiv) at room temperature. The mixture was then stirred for about 4 hours at room temperature.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-c894e82f0b25408c906ac247cadaa87a
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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