N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → 4-[4-Benzyloxy-2-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

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:32]=[CH:33][N:34]([CH3:36])C)=[N:28][CH:29]=[CH:30][CH:31]=1)#N.NC1C=C(OCC2C=CC=C(F)C=2)C=CC=1SC1C=CC(O)=CC=1>>[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:36]2[C:26]3[CH:31]=[CH:30][CH:29]=[N:28][C:27]=3[N:32]=[CH:33][N:34]=2)[CH:7]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine

HCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol2×

HCID 668086774-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 668083284-[4-Benzyloxy-2-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 27A and the product from Example 57A were reacted according to the procedure in Example 57E substituting the product of Example 27A for the product of Example 57D to provide the title compound which was isolated as the acetic acid salt (79 mg, 48%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 5.10 (s, 3H), 6.61-6.72 (m, 2H), 6.93 (d, J=9.56 Hz, 1H), 7.11 (d, J=8.46 Hz, 4H), 7.24 (s, 1H), 7.32-7.47 (m, 5H), 7.59-7.68 (m, 1H), 8.54 (s, 1H), 8.83 (d, J=9.56 Hz, 1H), 9.04 (s, 1H); ESI+ m/z 453 (M+H)+, ESI− m/z 451 (M−H)−.