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

HRID 607194Notes

Reaction equation

HRID 607194 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[S:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[O:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11].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>>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([S:18][C:17]2[CH:16]=[CH:15][C:4]([O:5][CH2:6][C:7]3[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=3)[C:10]#[N:11])=[CH:3][C:2]=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:24][CH:23]=1

Participants

4

Reactant 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 668085293-[3-Amino-4-(4-hydroxy-phenylsulfanyl)-phenoxymethyl]-benzonitrile2×HCID 668086774-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 668083423-[4-(4-Hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-phenoxymethyl]-benzonitrileYield 44%

Procedure

The product from Example 36H and the product from Example 57A were reacted according to the procedure in Example 57E substituting the product of Example 36H for the product of Example 57D to provide a solid which was triturated with methanol to provide the title compound (44 mg, 44%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.08 (s, 1H), 9.65 (s, 1H), 9.06 (s, 1H), 8.86 (s, 1H), 8.58 (s, 1H), 7.92 (s, 1H), 7.77-7.86 (m, 2H), 7.54-7.70 (m, J=7.72, 7.72 Hz, 2H), 7.28 (s, 1H), 7.07-7.19 (m, 3H), 6.97 (s, 1H), 6.63-6.72 (m, 2H), 5.18 (s, 2H); MS (ESI+) m/z 478.2 (M+H)+, (ESI−) m/z 476.1 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-9eb45e0908bd48a3b340d65b1d19af80
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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