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

HRID 607306Notes

Reaction equation

HRID 607306 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:34]=[CH:35][N:36]([CH3:38])C)=[N:28][C:29]([CH2:32][CH3:33])=[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:38]2[C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[N:28][C:27]=3[N:34]=[CH:35][N:36]=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 66808443N'-(3-Cyano-6-ethyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol2×

Product 1

HCID 668085814-[4-Benzyloxy-2-(7-ethyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 27A was reacted with the product from Example 145A using the procedure from Example 10F substituting the product from Example 27A for the product from Example 10E and substituting the product from Example 145A for the product from Example 10B to provide the title product. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.32 (t, J=7.72 Hz, 3H), 2.95 (q, J=7.72 Hz, 2H), 5.11 (s, 2H), 6.65 (d, J=8.82 Hz, 2H), 6.91-7.05 (m, 1H), 7.10 (d, J=8.46 Hz, 2H), 7.32-7.50 (m, 6H), 8.12 (d, J=6.99 Hz, 1H), 8.66-8.77 (m, 1H), 9.04 (d, J=8.82 Hz, 1H), 9.63 (s, 1H), 10.28 (s, 1H); MS (APCI) m/z 481 (M+H)+.

Sources & evidence

ORD record
ord-f71179df9738447388916e9845b7b68f
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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