N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide → N-[4-[2-[(7-cyclopropylpyrido[2,3-d]pyrimidin-4-yl)amino]-4-methyl-phenyl]sulfanylphenyl]acetamide

HRID 607229Notes

Reaction equation

HRID 607229 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1.C([C:22]1[C:23]([N:31]=[CH:32][N:33]([CH3:35])C)=[N:24][C:25]([CH:28]2[CH2:30][CH2:29]2)=[CH:26][CH:27]=1)#N.NC1C=C(C)C=CC=1SC1C=CC(O)=CC=1.C(C1C(N=CN(C)C)=NC(C)=CC=1)#N>>[CH:28]1([C:25]2[CH:26]=[CH:27][C:22]3[C:35]([NH:1][C:2]4[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=4[S:9][C:10]4[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=4)=[N:33][CH:32]=[N:31][C:23]=3[N:24]=2)[CH2:29][CH2:30]1

Participants

5

Reactant 4

HCID 43168935N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide2×HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 66808412N'-(3-Cyano-6-cyclopropyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 57394885N-[4-[2-[(7-cyclopropylpyrido[2,3-d]pyrimidin-4-yl)amino]-4-methyl-phenyl]sulfanylphenyl]acetamide

Procedure

The product from Example 7b was reacted with the product from Example 119A using the procedure from Example 102 substituting the product from Example 7b for the product from Example 6c and substituting the product from Example 119A for the product from Example 10B to provide the crude residue which was purified by trituration with methanol to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.13 (d, J=6.25 Hz, 4H), 2.02 (s, 3H), 2.22-2.38 (m, 1H), 2.31 (s, 3H), 7.07 (s, 2H), 7.20 (d, J=8.82 Hz, 2H), 7.30 (s, 1H), 7.50 (d, J=8.82 Hz, 2H), 7.56 (d, J=8.46 Hz, 1H), 8.49 (s, 1H), 8.68 (d, J=8.82 Hz, 1H), 9.99 (s, 2H); MS (ESI+) m/z 442 (M+H)+.

Workup

  1. customto provide the crude residue which
  2. customwas purified by trituration with methanol

Sources & evidence

ORD record
ord-05107f435f354978aaffea2af132e178
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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