Isopropyl isocyanate → HCID 59375071, 화합물

HRID 661936노트

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HRID 661936 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.[N:36]([CH:39]([CH3:41])[CH3:40])=[C:37]=[O:38]>C1COCC1>[CH:39]([NH:36][C:37](=[O:38])[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)([CH3:41])[CH3:40]

참가 물질

4

반응물 2

HCID 61277Isopropyl isocyanateHCID 59375043HCID 59375043, 화합물

생성물 1

HCID 59375071HCID 59375071, 화합물수율 16.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 7-(aminomethyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (Example 33-1, 30 mg, 0.065 mmol) and 2-isocyanatopropane (0.019 mL, 0.195 mmol) in THF (3 mL) was stirred at 40° C. overnight. The mixture was concentrated and purified by preparative HPLC. The appropriate effluent fractions were concentrated and partitioned between EtOAc and NaHCO3 (aq). The organic phase was dried and concentrated to provide 7-((3-isopropylureido)methyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (5.8 mg, 14%). 1H NMR (400 MHz, methanol-d4) δ 7.84 (1H, d, J=7.7 Hz), 7.77 (1H, d, J=7.5 Hz), 7.53-7.63 (2H, m), 7.38-7.51 (4 H, m), 7.30 (1H, dd, J=7.2, 1.7 Hz), 6.93-6.99 (2H, m), 6.85 (1H, dd, J=8.3, 1.4 Hz), 4.79-4.91 (2H, m), 4.33 (2H, s), 3.69-3.78 (1H, m), 1.79 (3H, s), 1.03 (6H, d, J=6.4 Hz). Mass spectrum m/z 546.3 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC
  3. concentrationThe appropriate effluent fractions were concentrated
  4. custompartitioned between EtOAc and NaHCO3 (aq)
  5. customThe organic phase was dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-25e02c6758134f2d950d208c151d2c00
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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