N'-(6-sec-Butyl-3-cyano-pyridin-2-yl)-N,N-dimethyl-formamidine → 4-[4-Benzyloxy-2-(7-sec-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607308Notes

Reaction equation

HRID 607308 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.[CH:24]([C:28]1[N:33]=[C:32]([N:34]=[CH:35]N(C)C)[C:31]([C:39]#[N:40])=[CH:30][CH:29]=1)([CH2:26][CH3:27])[CH3:25].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:39]2[C:31]3[CH:30]=[CH:29][C:28]([CH:24]([CH2:26][CH3:27])[CH3:25])=[N:33][C:32]=3[N:34]=[CH:35][N:40]=2)[CH:7]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 66808304N'-(6-sec-Butyl-3-cyano-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 668084074-[2-Amino-4-(4-methoxy-benzyloxy)-phenylsulfanyl]-phenolHCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidineHCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol2×

Product 1

HCID 668086444-[4-Benzyloxy-2-(7-sec-butyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 27A was reacted with the product from Example 140A using the procedure from Example 10F substituting the product from Example 27A for the product from Example 10E and substituting the product from Example 140A for the product from Example 10B to provide the title product. 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.82 (t, J=7.35 Hz, 3H), 1.30 (d, J=6.62 Hz, 3H), 1.58-1.73 (m, 1H), 1.75-1.87 (m, 1H), 2.89-3.08 (m, 1H), 5.11 (s, 2H), 6.67 (d, J=8.82 Hz, 2H), 6.85-7.03 (m, 1H), 7.11 (d, J=8.46 Hz, 2H), 7.30-7.50 (m, 6H), 7.56 (d, J=8.82 Hz, 1H), 8.56 (s, 1H), 8.75 (d, J=8.46 Hz, 1H), 9.64 (s, 1H), 9.95 (s, 1H); MS (APCI) m/z

Sources & evidence

ORD record
ord-278358a333bc47df825d1202e11b16d8
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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