Acetic Anhydride → 2-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

HRID 1853013노트

반응식

HRID 1853013 반응식
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:23][C:24]#[N:25])[CH2:22][NH:21][CH2:20]4)[CH:18]=3)[N:11]3[CH:26]=[CH:27][N:28]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.C1C[O:32][CH2:31][CH2:30]1.C(N(CC)CC)C.C(OC(=O)C)(=O)C>O>[C:31]([N:21]1[CH2:22][C:19]([CH2:23][C:24]#[N:25])([N:17]2[CH:18]=[C:14]([C:12]3[N:11]4[CH:26]=[CH:27][N:28]=[C:10]4[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][N:3]([CH3:2])[CH:7]=4)[N:13]=3)[CH:15]=[N:16]2)[CH2:20]1)(=[O:32])[CH3:30]

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 674570102-(3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride

생성물 1

HCID 866853142-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile수율 82.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (Example 62; 20 mg, 0.046 mmol) in THF (460 μL, 0.046 mmol) was added triethylamine (19 μL, 0.14 mmol) and acetic anhydride (5.7 mg, 0.056 mmol). After stirring at ambient temperature for 30 minutes, the reaction mixture was diluted in water. The reaction mixture was directly purified by reverse phase HPLC using a 0-100% acetonitrile/water gradient to afford 2-(1-acetyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile (15 mg, 0.038 mmol, 82% yield) as a fluffy white solid. MS (apci) m/z=402.2 (M+H).

후처리

  1. customThe reaction mixture was directly purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-db339df9ec0f41a3af9f80b17f03ec5a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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