Phenylacetyl chloride → HCID 18332602, compound

HRID 2268964Notes

Reaction equation

HRID 2268964 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.C(N(CC)CC)C.[C:32]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl.CCOC(C)=O>[C:32]1([CH2:38][C:39]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]3[N:15]=[C:14]([N:16]4[C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=5[N:18]=[CH:17]4)[CH:13]=[CH:12][N:11]=3)[CH3:8])[CH2:2]2)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 18332602HCID 18332602, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (28.2 mg, 0.087 mmol) in CH2Cl2 (1.0 mL) was added triethylamine (18 μL, 0.131 mmol) followed by phenylacetyl chloride (17 μL, 0.131 mmol) at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 5 h. The reaction mixture was diluted with EtOAc (10 mL), washed with saturated aqueous NaHCO3 followed by brine, and dried over Na2SO4. The crude product was purified by preparative thin layer chromatography (1:1 acetone:hexane) to yield 19.8 mg of the title compound. Presence of rotamers in Partial 1H NMR (500 MHz, CDCl3): δ 8.6 (s, 1H); 8.36 (d, J=5.3 Hz, 1H); 8.14 (m, 1H); 7.86 (m, 1H); 7.4-7.22 (aromatic H's, 7H); 6.78 (m, 1H); 4.67 (m, 1H); 3.73 (s, 2H); 1.31 (d, J=6.8 Hz, 1.5H); 1.11 (d, J=6.8 Hz, 1.5H). Mass spectrum 441.4 (ESI, M+1).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. customThe crude product was purified by preparative thin layer chromatography (1:1 acetone:hexane)

Sources & evidence

ORD record
ord-0c181e69e09f42c682aaf5af108b18dd
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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