3-(Trifluoromethyl)phenyl isocyanate → N-[4-Methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-N'-[3-(trifluoromethyl)-phenyl]urea

HRID 77708

반응식

HRID 77708 반응식
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[C:2]=[O:3].[CH3:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][C:16]=1[C:22]1[CH:30]=[C:29]2[C:25]([C:26]3[CH:34]=[N:33][CH:32]=[N:31][C:27]=3[NH:28]2)=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>C1COCC1.CO>[CH3:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]([NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)=[O:3])=[CH:17][C:16]=1[C:22]1[CH:30]=[C:29]2[C:25]([C:26]3[CH:34]=[N:33][CH:32]=[N:31][C:27]=3[NH:28]2)=[CH:24][CH:23]=1

참가 물질

6

반응물 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 81531DiisopropylethylamineHCID 690464994-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline

생성물 1

HCID 59774720N-[4-Methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-N'-[3-(trifluoromethyl)-phenyl]urea

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To 1-isocyanato-3-(trifluoromethyl)benzene (8.7 μl, 0.062 mmol) was added a solution of 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline (17.0 mg, 0.062 mmol) and DIPEA (16 μL, 0.089 mmol) in THF (0.4 mL). The reaction was stirred at ambient temperature until LCMS indicated complete reaction, typically 3-4 hours. The reaction mixture was diluted to a total of 2 mL with THF and MeOH and purified by preparative LCMS to recover the product as a TFA salt (16.7 mg, 46.9%). 1H NMR (400 MHz, CDCl3): δ 13.0 (bs, 1H), 9.65 (s, 1H), 9.15 (s, 2H), 8.93 (s, 1H), 8.37 (d, 1H), 8.01 (s, 1H), 7.4-7.6 (m, 5H), 7.2-7.4 (m, 3H), 2.21 (s, 3H). MS (EI) m/z=462 (M+H).

후처리

  1. customreaction, typically 3-4 hours
  2. custompurified by preparative LCMS
  3. customto recover the product as a TFA salt (16.7 mg, 46.9%)

출처 및 근거

ORD 기록
ord-ef003d29ce93406f9f5dfd9f2cc70902
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

연결된 노트

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