Lithium Hydroxide → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamine

HRID 1157534

반응식

HRID 1157534 반응식
Cl.FC(F)(F)C([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]5[O:39][CH:38]=[N:37][CH:36]=5)[CH:30]=4)[N:23]=3)=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]3[N:14]=2)[CH:8]=1)=O.[Li+].[OH-]>C1COCC1.O>[NH2:6][C:7]1[CH:8]=[C:9]([C:13]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([C:35]5[O:39][CH:38]=[N:37][CH:36]=5)[CH:30]=4)[N:23]=3)=[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]3[N:14]=2)[CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 866310832,2,2-Trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide hydrochloride

생성물 1

HCID 577371674-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamine수율 98%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2,2,2-trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide hydrochloride (0.68 g, 1.26 mmol) and LiOH (69 mg, 1.64 mmol) in THF (15 mL) and water (5 mL) was stirred for 6 h at 50° C. The reaction was extracted with DCM. The combined organic phases were dried over MgSO4 and evaporated down to give the title compound as a tan solid, (0.55 g, 98% yield). 1H NMR (400 MHz, d6-DMSO): δ 9.73 (s, 1H), 8.82 (d, J=6.7 Hz, 1H), 8.60 (d, J=8.9 Hz, 1H), 8.42 (s, 1H), 8.29 (d, J=5.3 Hz, 1H), 8.24 (s, 1H), 7.76 (d, J=7.7 Hz, 1H), 7.61 (s, 1H), 7.35-7.44 (m, 3H), 7.10-7.19 (m, 2H), 6.83 (s, 1H), 6.69-6.73 (m, 2H), 6.58 (d, J=5.3 Hz, 1H), 5.30 (bs, 2H) ppm. ES-LC/MS m/z=446 [M+H]+.

후처리

  1. extractionThe reaction was extracted with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customevaporated down

출처 및 근거

ORD 기록
ord-cc0260908af64bb2b100c1d50ae6b279
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807673B2

연결된 노트

불러오는 중…