4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-[2-[(7-Cyclopropylpyrido[2,3-d]pyrimidin-4-yl)amino]-4-methyl-phenyl]sulfanylphenol

HRID 607228Notes

Reaction equation

HRID 607228 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]([OH:16])=[CH:12][CH:11]=1.C([C:19]1[C:20]([N:28]=[CH:29][N:30]([CH3:32])C)=[N:21][C:22]([CH:25]2[CH2:27][CH2:26]2)=[CH:23][CH:24]=1)#N.C(C1C(N=CN(C)C)=NC(C)=CC=1)#N>>[CH:25]1([C:22]2[CH:23]=[CH:24][C:19]3[C:32]([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]([OH:16])=[CH:12][CH:11]=4)=[N:30][CH:29]=[N:28][C:20]=3[N:21]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 3

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 573966514-[2-[(7-Cyclopropylpyrido[2,3-d]pyrimidin-4-yl)amino]-4-methyl-phenyl]sulfanylphenol

Procedure

The product from Example 6c was reacted with the product from Example 119A using the procedure from Example 102 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: 1.05-1.22 (m, J=1.84 Hz, 4H), 2.24-2.39 (m, 1H), 2.29 (s, 3H), 6.73 (d, J=8.82 Hz, 2H), 6.91 (d, J=8.09 Hz, 1H), 7.04 (dd, J=8.09, 1.47 Hz, 1H), 7.17 (d, J=8.82 Hz, 2H), 7.25 (s, 1H), 7.57 (d, J=8.82 Hz, 1H), 8.49 (s, 1H), 8.71 (d, J=8.46 Hz, 1H), 9.74 (s, 1H), 9.92 (s, 1H); MS (ESI)+ m/z 401 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-9387709d280e4a50b84611ca9c8577a5
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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