Pyrrolidine → HCID 59511429, compound

HRID 1157552Notes

Reaction equation

HRID 1157552 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[C:19]([C:27]4[CH:28]=[C:29]([NH:33]C(=O)C(F)(F)F)[CH:30]=[CH:31][CH:32]=4)=[N:20][N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=34)[CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1.[NH:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[NH2:33][C:29]1[CH:28]=[C:27]([C:19]2[C:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][CH2:2][N:40]5[CH2:44][CH2:43][CH2:42][CH2:41]5)[CH:6]=4)[N:17]=3)=[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]3[N:20]=2)[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 59513692HCID 59513692, compound

Product 1

HCID 59511429HCID 59511429, compoundYield 74%

Conditions

Temperature
50 °C

Procedure

N-(3-{3-[2-({3-[(2-Chloroethyl)oxy]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}phenyl)-2,2,2-trifluoroacetamide (0.5 g, 0.85 mmol) was dissolved in pyrrolidine and heated to 50° C. for 18 h. Upon completion the reaction was then cooled and absorbed directly onto silica gel. Purification via column chromatography using a 0-20% gradient of EtOAc/MeOH w/NH4OH afforded the desired product as a yellow solid, 310 mg, 74% yield. ES-LC/MS m/z 492 [M+H]+.

Workup

  1. temperatureUpon completion the reaction was then cooled
  2. customabsorbed directly onto silica gel
  3. customPurification via column chromatography

Sources & evidence

ORD record
ord-c797759c9af5446f8a9016a60457a15d
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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