2-(4-Methoxyphenoxy)-5-methylaniline → (7-Cyclopropyl-pyrido[2,3-d]pyrimidin-4-yl)-[2-(4-methoxy-phenoxy)-5-methyl-phenyl]-amine

HRID 607233Notes

Reaction equation

HRID 607233 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[NH2:15])=[CH:5][CH:4]=1.C([C:20]1[C:21]([N:29]=[CH:30][N:31]([CH3:33])C)=[N:22][C:23]([CH:26]2[CH2:28][CH2:27]2)=[CH:24][CH:25]=1)#N.NC1C=C(C)C=CC=1SC1C=CC(O)=CC=1.C(C1C(N=CN(C)C)=NC(C)=CC=1)#N>>[CH:26]1([C:23]2[CH:24]=[CH:25][C:20]3[C:33]([NH:15][C:9]4[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=4[O:7][C:6]4[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[N:31][CH:30]=[N:29][C:21]=3[N:22]=2)[CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 176056672-(4-Methoxyphenoxy)-5-methylaniline2×HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 66808412N'-(3-Cyano-6-cyclopropyl-pyridin-2-yl)-N,N-dimethyl-formamidine2×HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

Product 1

HCID 66809836(7-Cyclopropyl-pyrido[2,3-d]pyrimidin-4-yl)-[2-(4-methoxy-phenoxy)-5-methyl-phenyl]-amine

Procedure

The product from Example 116B was reacted with the product from Example 119A using the procedure from Example 102 substituting the product from Example 116B for the product from Example 6c and substituting the product from Example 119A for the product from Example 10B to provide the crude residue which was purified by trituration with methanol to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.02-1.20 (m, J=6.25 Hz, 4H), 2.21-2.37 (m, 1H), 2.31 (s, 3H), 3.66 (s, 3H), 6.75-6.92 (m, 5H), 7.06 (dd, J=8.64, 0.92 Hz, 1H), 7.37 (s, 1H), 7.51 (d, J=8.46 Hz, 1H), 8.49 (s, 1H), 8.63 (d, J=8.82 Hz, 1H), 9.74 (s, 1H); MS (ESI)+ m/z 399 (M+H)+.

Workup

  1. customto provide the crude residue which
  2. customwas purified by trituration with methanol

Sources & evidence

ORD record
ord-1650377cfcbc4d8fb47431e13602a229
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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