Acetic Anhydride → HCID 59375109, 화합물

HRID 661934노트

반응식

HRID 661934 반응식
[NH2:1][CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[C:26]5=[O:34])[C:20]=4[CH3:35])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C1COCC1>[C:36]([NH:1][CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:33][C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[C:26]5=[O:34])[C:20]=4[CH3:35])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1)(=[O:38])[CH3:37]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 59375043HCID 59375043, 화합물

생성물 1

HCID 59375109HCID 59375109, 화합물수율 36.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of crude 7-(aminomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 33-1, 60 mg, 0.065 mmol) and TEA (23 μL, 0.163 mmol) in THF (1.3 mL) was treated with acetic anhydride (7.4 μL, 0.078 mmol) and the mixture was stirred at rt overnight. The mixture was concentrated and the residue was purified by preparative HPLC. The appropriate effluent fractions were concentrated and the residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated to provide 7-(acetamidomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as an off-white solid (12 mg, 36%). 1H NMR (400 MHz, DMSO-d6) δ 11.51 (1H, s), 8.29-8.45 (1H, m), 8.18 (1H, br. s.), 8.01 (1H, d, J=7.9 Hz), 7.81 (1H, d, J=7.5 Hz), 7.69 (2H, d, J=4.0 Hz), 7.60-7.65 (2H, m), 7.57 (1H, ddd, J=7.9, 4.2, 4.0 Hz), 7.50 (2H, t, J=7.8 Hz), 7.34 (1H, dd, J=7.7, 1.1 Hz), 6.94-7.06 (2H, m), 6.87 (1H, dd, J=8.3, 1.4 Hz), 4.90-5.04 (2H, m), 4.35 (2H, t, J=5.2 Hz), 1.89 (3H, s), 1.84 (3H, s). Mass spectrum m/z 503.2 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC
  3. concentrationThe appropriate effluent fractions were concentrated
  4. customthe residue was partitioned between NaHCO3 (aq) and EtOAc
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eae1c1bc3c1f400394358b0c5075555f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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