3-Methylbenzoyl chloride → HCID 178425290, compound

HRID 1162157Notes

Reaction equation

HRID 1162157 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[NH:20][N:19]=[C:18]([CH3:21])[CH:17]=3)[CH:12]=[C:11]([N:22]3[CH2:25][CH2:24][CH2:23]3)[N:10]=2)=[CH:4][CH:3]=1.[C:26]1([CH3:35])[CH:31]=[CH:30][CH:29]=[C:28]([C:32](Cl)=[O:33])[CH:27]=1>N1C=CC=CC=1>[CH3:21][C:18]1[CH:17]=[C:16]([NH:15][C:13]2[CH:12]=[C:11]([N:22]3[CH2:23][CH2:24][CH2:25]3)[N:10]=[C:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32](=[O:33])[C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([CH3:35])[CH:27]=4)=[CH:3][CH:4]=3)[N:14]=2)[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 743753-Methylbenzoyl chlorideHCID 178428240HCID 178428240, compound

Product 1

HCID 178425290HCID 178425290, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Aminophenylthio)-6-(azetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)pyrimidin-4-amine (200 mg, 0.57 mmol) was taken up in pyridine (2 mL) and m-toluoyl chloride (0.187 mL, 1.42 mmol) was added dropwise at room temperature. After 15 minutes the reaction mixture was concentrated in vacuo and the residue taken up in methanol (3 mL). Sodium methoxide (25% w/w solution in MeOH, 1 mL) was added and the resulting cloudy solution stirred at room temperature for 15 minutes. The reaction mixture was purified directly by chromatography (silica, 5-100% EtOAc-petrol gradient elution) to give the title compound (89 mg, 33%) as a white solid. 1H NMR: (400 MHz, DMSO) 1.99 (3H, brs), 2.31 (2H, qn), 2.42 (3H, s), 3.88 (4H, t), 5.39 (1H, brs), 5.67 (1H, vbrs), 7.43-7.46 (2H, m), 7.54 (2H, d), 7.73-7.76 (2H, m), 7.91 (2H, d), 9.23 (1H, brs), 10.42 (1H, s), 11.67 (1H, brs). ES+472.

Workup

  1. concentrationAfter 15 minutes the reaction mixture was concentrated in vacuo
  2. additionSodium methoxide (25% w/w solution in MeOH, 1 mL) was added
  3. customThe reaction mixture was purified directly by chromatography (silica, 5-100% EtOAc-petrol gradient elution)

Sources & evidence

ORD record
ord-79af1109e3ec45b3b0353f22533e7271
Source dataset
uspto-grants-2010_10
Patent number
US07820685B2

Reaction notes

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