N-Methylallylamine → HCID 59513875, compound

HRID 1160009Notes

Reaction equation

HRID 1160009 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[C:20]([C:32]4[CH:33]=[C:34]([NH:38]C(=O)C5C(F)=CC=CC=5F)[CH:35]=[CH:36][CH:37]=4)=[N:21][N:22]4[CH:27]=[C:26](C(F)(F)F)[CH:25]=[CH:24][C:23]=34)[CH:16]=[CH:15][N:14]=2)[CH:9]=[CH:10][CH:11]=1.ClCCO[C:54]1[CH:55]=C(NC2N=C(C3C(C4C=C(NC(=O)C(F)(F)F)C=CC=4)=NN4C=CC=CC=34)C=CN=2)C=C[CH:59]=1.CNCC=C>>[NH2:38][C:34]1[CH:33]=[C:32]([C:20]2[C:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:8]4[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:55][CH:54]=[CH2:59])[CH:7]=4)[N:18]=3)=[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]3[N:21]=2)[CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 69391N-MethylallylamineHCID 59513692HCID 59513692, compound2×HCID 59513849HCID 59513849, compound

Product 1

HCID 59513875HCID 59513875, compound

Procedure

The title compound can be prepared from N-(3-{3-[2-({3-[(2-chloroethyl)oxy]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)-2,2,2-trifluoroacetamide (obtained according to the procedure described in Example 136, Step C) through a two step process consisting of treatment of N-(3-{3-[2-({3-[(2-chloroethyl)oxy]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)-2,2,2-trifluoroacetamide with N-methyl-2-propen-1-amine to give 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-({2-[methyl(2-propen-1-yl)amino]ethyl}oxy)phenyl]-2-pyrimidinamine, which in turn can be treated with 2,6-difluorobenzoyl chloride in THF and TEA to give the product as a solid. ES-LCMS m/z 632 (M+H).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-9ad7a32e477649d2b88f1e7262c3057e
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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