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

HRID 607197Notes

Reaction equation

HRID 607197 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[S:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C([C:28]1[C:29]([N:34]=[CH:35][N:36]([CH3:38])C)=[N:30][CH:31]=[CH:32][CH:33]=1)#N.NC1C=C(OCC2C=CC=C(F)C=2)C=CC=1SC1C=CC(O)=CC=1>>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([S:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)=[C:2]([NH:1][C:38]2[C:28]3[CH:33]=[CH:32][CH:31]=[N:30][C:29]=3[N:34]=[CH:35][N:36]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 668085064-[2-Amino-4-(3-methoxy-benzyloxy)-phenylsulfanyl]-phenol2×HCID 668086774-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 668083654-[4-(3-Methoxy-benzyloxy)-2-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenolYield 45%

Procedure

The product from Example 31A and the product from Example 57A were reacted according to the procedure in Example 57E substituting the product of Example 31A for the product of Example 57D to provide a solid which was triturated with methanol to provide the title compound (38 mg, 45%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.07 (s, 1H), 9.63 (s, 1H), 9.07 (s, 1H), 8.86 (d, J=7.72 Hz, 1H), 8.59 (s, 1H), 7.64 (s, 1H), 7.23-7.36 (m, 2H), 7.16 (dd, J=8.64, 1.65 Hz, 1H), 7.07-7.13 (m, 2H), 6.93-7.05 (m, 3H), 6.89 (dd, J=8.27, 2.02 Hz, 1H), 6.61-6.71 (m, 2H), 5.08 (s, 2H), 3.75 (s, 3H); MS (ESI+) m/z 483.2 (M+H)+, (ESI−) m/z 481.2 (M−H)−.

Workup

  1. customto provide a solid which
  2. customwas triturated with methanol

Sources & evidence

ORD record
ord-99180858af3d4474b0d073477a386c00
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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