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

HRID 607185Notes

Reaction equation

HRID 607185 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:35]=[CH:36][N:37]([CH3:39])C)=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=1)#N.NC1C=C(OCC2C=CC(OC)=CC=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:39]2[C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[N:30][C:29]=3[N:35]=[CH:36][N:37]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 668084074-[2-Amino-4-(4-methoxy-benzyloxy)-phenylsulfanyl]-phenolHCID 668085064-[2-Amino-4-(3-methoxy-benzyloxy)-phenylsulfanyl]-phenol2×HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 602047744-[4-(3-Methoxy-benzyloxy)-2-(7-methyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenolYield 26%

Procedure

The product of Example 31A was reacted with the product of Example 10B using the procedure of Example 10F substituting the product of Example 31A for the product of Example 10E to provide a solid which was triturated with methanol to provide the title compound (24 mg, 26%). 1H NMR (300 MHz, DMSO-D6) δ ppm 9.93 (s, 1H), 9.63 (s, 1H), 8.71 (d, J=8.09 Hz, 1H), 8.55 (s, 1H), 7.53 (d, J=8.09 Hz, 1H), 7.26-7.35 (m, 2H), 7.15 (d, J=8.46 Hz, 1H), 7.07-7.13 (m, 2H), 6.98-7.04 (m, J=5.15 Hz, 2H), 6.96 (s, 1H), 6.90 (dd, J=8.09, 2.57 Hz, 1H), 6.62-6.71 (m, 2H), 5.08 (s, 2H), 3.75 (s, 3H), 2.67 (s, 3H); MS (ESI+) m/z 497.2 (M+H)+ (ESI−) m/z 495.2 (M−H)−.

Workup

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

Sources & evidence

ORD record
ord-47423371bdff44a48229b1d88ff76aa4
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

Loading…