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

HRID 607198Notes

Reaction equation

HRID 607198 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

4

Reactant 3

HCID 66808319N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 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)−.

Sources & evidence

ORD record
ord-2a0415099af243c09d862306628765cf
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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