Pyrrolidine → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamine

HRID 1157598Notes

Reaction equation

HRID 1157598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[C:16]([C:24]4[CH:25]=[C:26]([NH:30]C(=O)C(F)(F)F)[CH:27]=[CH:28][CH:29]=4)=[N:17][N:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=34)[CH:12]=[CH:11][N:10]=2)=[CH:4][C:3]=1[O:37][CH2:38][CH2:39]Cl.[NH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>>[NH2:30][C:26]1[CH:25]=[C:24]([C:16]2[C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:37][CH2:38][CH2:39][N:41]5[CH2:45][CH2:44][CH2:43][CH2:42]5)[CH:4]=4)[N:14]=3)=[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]3[N:17]=2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57737180N-(3-{3-[2-({4-Chloro-3-[(2-chloroethyl)oxy]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 577372284-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(4-chloro-3-{[2-(1-pyrrolidinyl)ethyl]oxy}phenyl)-2-pyrimidinamineYield 50%

Procedure

The compound was synthesized from N-(3-{3-[2-({4-chloro-3-[(2-chloroethyl)oxy]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)-2,2,2-trifluoroacetamide and pyrrolidine using procedure outlined in Example 10, Step D, to afford a solid in 50% yield. ES-LC/MS m/z 526-[M+H]+.

Workup

  1. customto afford a solid in 50% yield

Sources & evidence

ORD record
ord-e225a31cb9604cf994bfeb6d1542f948
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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