2-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine → (7-Cyclopropyl-pyrido[2,3-d]pyrimidin-4-yl)-[2-(4-fluoro-phenylsulfanyl)-5-methyl-phenyl]-amine

HRID 607235Notes

Reaction equation

HRID 607235 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[NH2:16])=[CH:4][CH:3]=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:16][C:10]4[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=4[S:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[N:30][CH:29]=[N:28][C:20]=3[N:21]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 4

HCID 431689322-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine2×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 66808336(7-Cyclopropyl-pyrido[2,3-d]pyrimidin-4-yl)-[2-(4-fluoro-phenylsulfanyl)-5-methyl-phenyl]-amine

Procedure

2-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine was reacted with the product from Example 119A using the procedure from Example 102 substituting 2-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine 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: 0.96-1.19 (m, J=6.25 Hz, 4H), 2.22-2.42 (m, 1H), 2.33 (s, 3H), 7.02-7.28 (m, 6H), 7.33 (s, 1H), 7.56 (d, J=8.46 Hz, 1H), 8.46 (s, 1H), 8.66 (d, J=8.09 Hz, 1H), 10.03 (s, 1H); MS (ESI)+ m/z 403 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-e75693b6c8a04afcbb09a25ff9c180f4
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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