Benzoyl chloride, 3-chloro- → HCID 59548760, compound

HRID 1810970Notes

Reaction equation

HRID 1810970 reaction equation
[NH2:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:24])[CH2:16][N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([NH:1][C:2]1[C:3]([N:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:24])[CH2:16][N:17]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[N:18]3)[CH2:13][CH2:14]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1)=[O:30]

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 81531DiisopropylethylamineHCID 59548857HCID 59548857, compound

Product 1

HCID 59548760HCID 59548760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(3-amino-5-chloro-pyridin-2-yl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone (0.040 g, 0.11 mmol) in methylene chloride (2 mL) is added 3-chlorobenzoyl chloride (0.020 mL, 0.160 mmol) followed by of N,N-diisopropylethylamine (0.045 mL, 0.25 mmol). The mixture is stirred at room temperature for 3 days. The mixture is concentrated under a stream of nitrogen and the residue is purified by preparative reverse phase HPLC to provide, after removal of the eluent under reduced pressure, 0.030 g of 3-chloro-N-(5-chloro-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-pyridin-3-yl)-benzamide as a white solid in 53% yield. MS; MH+=487.7

Workup

  1. concentrationThe mixture is concentrated under a stream of nitrogen
  2. customthe residue is purified by preparative reverse phase HPLC
  3. customto provide
  4. customafter removal of the eluent under reduced pressure, 0.030 g of 3-chloro-N-(5-chloro-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-pyridin-3-yl)-benzamide as a white solid in 53% yield

Sources & evidence

ORD record
ord-db762269aec84f8dad15144fc67dc5d2
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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