(2-(Methylthio)ethyl)amine → 2-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylthio)ethyl]benzamide

HRID 1864071Notes

Reaction equation

HRID 1864071 reaction equation
[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([O:28]CC)=O)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:10]=2)=[N:6][CH:7]=1.[CH3:35][S:36][CH2:37][CH2:38][NH2:39]>>[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=2[C:26]([NH:39][CH2:38][CH2:37][S:36][CH3:35])=[O:28])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 87697(2-(Methylthio)ethyl)amineHCID 66941025Ethyl 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}benzoate

Product 1

HCID 579741382-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylthio)ethyl]benzamide

Procedure

Ethyl 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}benzoate (200 mg, 0.51 mmoles) and 2-(methylthio)ethylamine (2 mL) were heated at 120° C. for 48 h. The reaction mixture was concentrated to dryness under vacuum and the title compound was purified by flash chromatography on silica gel (ethyl acetate containing 0.1% triethylamine). MS: M(C26H31FN6O2S)=510.2, (M+H)+=511.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under vacuum
  2. customthe title compound was purified by flash chromatography on silica gel (ethyl acetate containing 0.1% triethylamine)

Sources & evidence

ORD record
ord-6ef4ba73f277439dbdc6764826cf2014
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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