Benzoyl chloride → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-benzoylamino-indol-1-yl)-amide

HRID 2382111Notes

Reaction equation

HRID 2382111 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([NH:20][C:21]([C:23]1[C:24]([CH3:36])=[N:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)=[N:27][CH:28]=1)=[O:22])[CH:15]=[CH:14]2.C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([NH:20][C:21]([C:23]1[C:24]([CH3:36])=[N:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)=[N:27][CH:28]=1)=[O:22])[CH:15]=[CH:14]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 591999982-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide

Product 1

HCID 591999582-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-benzoylamino-indol-1-yl)-amideYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl chloride (0.85 mmol) in anhydrous DCM (2 mL) is added drop-wise to a solution of 4-methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide (0.47 mmol) and triethylamine (1.41 mmol) in anhydrous DCM (16 mL) and the mixture is stirred at rt overnight. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc (25 mL), and washed with water (2×20 mL) and brine (10 mL). The organic layer is dried (Na2SO4), filtered and concentrated. The residue is triturated with EtOAc to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-benzoylamino-indol-1-yl)-amide (95 mg, 43%) as a solid. MS: 466 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 2.99(s, 3H), 6.72(d, H), 7.38-7.48(m, H), 7.48-7.80(m, 6H), 7.83-8.016(m, 3H), 8.07-8.20(m, H), 8.23-8.35(m, 2H), 9.24(s, H), 10.25(br, H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (25 mL)
  3. washwashed with water (2×20 mL) and brine (10 mL)
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is triturated with EtOAc

Sources & evidence

ORD record
ord-69dcbe9851d54eafbe3745eb45bebba4
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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