2,3-Difluorobenzoyl chloride → HCID 20800936, compound

HRID 1071451Notes

Reaction equation

HRID 1071451 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:10]2[CH:26]=[CH:27][CH:28]=[CH:29][C:9]=2[N:8]=1)[CH2:2][CH2:3][CH3:4].[F:30][C:31]1[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34]>C1(C)C=CC=CC=1.ClC(Cl)C>[CH2:1]([N:5]([CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C:10]2[CH:26]=[CH:27][CH:28]=[CH:29][C:9]=2[N:8]=1)[C:33](=[O:34])[C:32]1[CH:36]=[CH:37][CH:38]=[C:39]([F:40])[C:31]=1[F:30])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 5195492,3-Difluorobenzoyl chlorideHCID 69741519HCID 69741519, compound

Product 1

HCID 20800936HCID 20800936, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 0.9 g (1.7 mmole) of compound D was treated with 10 mL of butyl amine in 50 mL of acetonitrile at room temperature for 2 hr. The resulting solution was concentrated and partitioned between ethyl acetate and 1N NaOH. The organic layer was dried over anhydrous Na2SO4 and concentrated to yield 0.55 g of Butyl-[1-(2-piperidin-1-ylmethyl-benzyl)-1H-benzoimidazol-2-ylmethyl]-amine. 1H NMR (300 MHz, CDCl3) 7.8 (d, 1H), 7.2 (m, 5H), 7.05 (d, 1H), 6.4 (d, 1H), 5.8 (s, 2H), 4.0 (s, 2H), 3.6 (s, 2H), 2.6 (t, 2H), 1.2-1.6 (m, 14H), 0.8 (t, 3H). A quantity of 0.1 mL of a 0.2 M solution of Butyl-[1-(2-piperidin-1-ylmethyl-benzyl)-1H-benzoimidazol-2-ylmethyl]-amine in toluene is treated with 0.15 mL of a 0.2 M solution of 2,3-Difluoro-benzoyl chloride in dichloroethane at room temperature for 1 hr. The resulting mixture was chromatographed on SiO2 with ethyl acetate to yield 9 mg of N-Butyl-2,3-difluoro-N-[1-(2-piperidin-1-ylmethyl-benzyl)-1H-benzoimidazol-2-ylmethyl]-benzamide. LCMS MF=C32H36F2N4O MW=530.6 found 531. B. N-Butyl-2,3-difluoro-N-[1-(4-piperidin-1-yl-but-2-Enyl)-1H-benzoimidazol-2-ylmethyl]-benzamide

Workup

  1. customThe resulting mixture was chromatographed on SiO2 with ethyl acetate

Sources & evidence

ORD record
ord-4bc6ea4d643a4b2e85da25bec380521f
Source dataset
uspto-grants-2005_06
Patent number
US06906075B2

Reaction notes

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