4-[2-Amino-4-(4-methoxy-benzyloxy)-phenylsulfanyl]-phenol → 4-[4-Benzyloxy-2-(7-cyclohexyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607307Notes

Reaction equation

HRID 607307 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[S:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C([C:26]1[C:27]([N:38]=[CH:39][N:40]([CH3:42])C)=[N:28][C:29]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:30][CH:31]=1)#N.NC1C=C(OCC2C=CC(OC)=CC=2)C=CC=1SC1C=CC(O)=CC=1.C(C1C(N=CN(C)C)=NC(C)=CC=1)#N>>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([S:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[C:2]([NH:1][C:42]2[C:26]3[CH:31]=[CH:30][C:29]([CH:32]4[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]4)=[N:28][C:27]=3[N:38]=[CH:39][N:40]=2)[CH:7]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 668084074-[2-Amino-4-(4-methoxy-benzyloxy)-phenylsulfanyl]-phenolHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 66808582N'-(3-Cyano-6-cyclohexyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol2×

Product 1

HCID 668086374-[4-Benzyloxy-2-(7-cyclohexyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 27A was reacted with the product from Example 135A using the procedure from Example 10F substituting the product from Example 27A for the product from Example 10E and substituting the product from Example 135A for the product from Example 10B to provide the title product. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.23-1.51 (m, 4H), 1.53-1.79 (m, 4H), 1.80-2.00 (m, 2H), 2.77-3.02 (m, 1H), 5.10 (s, 2H), 6.67 (d, J=8.46 Hz, 2H), 6.88-7.01 (m, 1H), 7.11 (d, J=8.82 Hz, 2H), 7.22-7.31 (m, 1H), 7.32-7.49 (m, 6H), 7.56 (d, J=7.72 Hz, 1H), 8.55 (s, 1H), 8.73 (d, J=8.09 Hz, 1H), 9.94 (s, 1H); MS (APCI) m/z 535 (M+H)+.

Sources & evidence

ORD record
ord-e2c2d8de7ce44b83aa3f09e458b308ff
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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