3,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline → N4-[3,5-Difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-pyridin-4-yl-pyrimidine-2,4-diamine

HRID 16447Notes

Reaction equation

HRID 16447 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[C:6]([F:18])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[CH:17][C:10]=12.Cl[C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[N:24]=[C:23]([NH2:33])[N:22]=1>>[F:18][C:6]1[CH:5]=[C:4]([NH:19][C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[N:24]=[C:23]([NH2:33])[N:22]=2)[CH:3]=[C:2]([F:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][CH:16]=[CH:17][C:10]=12

Participants

3

Reactant 2

HCID 179792873,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)anilineHCID 223242864-Chloro-6-(pyridin-4-yl)pyrimidin-2-amine

Product 1

HCID 58733336N4-[3,5-Difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-6-pyridin-4-yl-pyrimidine-2,4-diamine

Procedure

Analogously to example 25, the title compound is synthesized from 100 mg (0.36 mmol) of [3,5-difluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine (from example XXXIV) and 87 mg (0.36 mmol) of 4-chloro-6-(4-pyridinyl)-2-pyrimidineamine (from example XXIX). Purification by preparative HPLC gives the product.

Workup

  1. customPurification by preparative HPLC
  2. customgives the product

Sources & evidence

ORD record
ord-d7faeaf62c1341bcba7b47b9ba9ccf35
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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