Acetyl chloride → 1-(4-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazol-1-yl)ethanone

HRID 594972노트

반응식

HRID 594972 반응식
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:19]=[N:18][N:17]([C:31](=[O:33])[CH3:32])[CH:16]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67112034HCID 67112034, 화합물

생성물 1

HCID 683769121-(4-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazol-1-yl)ethanone

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(2-fluorobenzyl)-N-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (56 mg, 0.18 mmol), (Example 88), in DCM (2 mL) were added triethylamine (384, 1.5 eq) and acetyl chloride (154, 1.2 eq). After stirring for 30 min at rt, the reaction mixture was quenched with water. The aqueous phase was extracted with DCM and the combined organic phases dried over sodium sulfate and concentrated in vacuo. The residue was purified with the preparative HPLC to give the title product. 1H NMR (d6-DMSO) δ 10.25 (s, 1H), 9.03 (s, 1H), 8.67 (s, 1H), 8.15 (s, 1H), 8.04 (s, 1H), 7.41-7.31 (m, 2H), 7.26-7.12 (m, 2H), 5.60 (s, 2H), 2.63 (s, 3H); LC-MS method B, (ES+) 352.0, RT=9.09 min.

후처리

  1. customthe reaction mixture was quenched with water
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organic phases dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with the preparative HPLC

출처 및 근거

ORD 기록
ord-05945261ccb94dabb37e0ecbd3db1398
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242987B2

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