4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-(2-(7-Cyclopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-methylphenoxy)phenol

HRID 607232Notes

Reaction equation

HRID 607232 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=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.NC1C=C(C)C=CC=1SC1C=CC(O)=CC=1.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:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=4[O:4][C:5]4[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=4)=[N:30][CH:29]=[N:28][C:20]=3[N:21]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 4

HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 668083884-(2-Amino-4-methylphenoxy)phenol2×HCID 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 602047934-(2-(7-Cyclopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-methylphenoxy)phenol

Procedure

The product from Example 122b was reacted with the product from Example 119A using the procedure from Example 102 substituting the product from Example 122b 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: 1.03-1.18 (m, J=6.25 Hz, 4H), 2.20-2.35 (m, 1H), 2.30 (s, 3H), 6.57-6.85 (m, 5H), 7.03 (dd, J=8.27, 1.65 Hz, 1H), 7.36 (d, J=1.84 Hz, 1H), 7.52 (d, J=8.46 Hz, 1H), 8.50 (s, 1H), 8.65 (d, J=8.46 Hz, 1H), 9.18 (s, 1H), 9.70 (s, 1H); MS (ESI)+ m/z 385 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-ce2e3f67e2d147948659ba42def751e6
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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