Acetyl chloride → HCID 57968771, 화합물

HRID 1483762노트

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HRID 1483762 반응식
NC[C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:11]3[B:12]([OH:15])[O:13][CH2:14][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1.[CH3:20][CH2:21][N:22](CC)CC.C(Cl)(=[O:29])C>C(Cl)Cl>[OH:15][B:12]1[C:11]2[CH:16]=[CH:17][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([NH:22][C:21](=[O:29])[CH3:20])=[CH:19][CH:18]=3)=[CH:9][C:10]=2[CH2:14][O:13]1

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57968923Crisaborole intermediate

생성물 1

HCID 57968771HCID 57968771, 화합물수율 94.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 20 mL scintillation vial containing 5-(4-aminomethyl-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol (150 mg, 0.59 mmol, 1.0 eq.) in DCM (5.0 mL) was added Et3N (180 μL, 1.3 mmol, 2.2 eq.), followed by acetyl chloride (84 μL, 1.2 mmol, 2.0 eq.). The mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure. The residue was applied to silica chromatography eluting with MeOH/DCM (0:100 to 10:90) to give N-[4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-phenyl]-acetamide as a white solid. LCMS (m/z) 298 (M+H); 1H NMR (CHLOROFORM-d) δ: 7.55 (d, J=8.0 Hz, 1H), 7.11 (d, J=8.6 Hz, 2H), 6.74-6.83 (m, 3H), 6.68 (d, J=1.4 Hz, 1H), 4.79 (s, 2H), 4.21 (d, J=5.8 Hz, 2H), 1.84 (s, 3H). Amount obtained, 165 mg, 94.3% yield.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washeluting with MeOH/DCM (0:100 to 10:90)

출처 및 근거

ORD 기록
ord-fec4e0014f9a483fa0c9f0220db95326
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416146B2

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