3-(Trifluoromethyl)phenyl isocyanate → N-[4-Methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)phenyl]-N'-[3-(trifluoromethyl)-phenyl]urea

HRID 77709

반응식

HRID 77709 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:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]1[N:31]=[CH:32][N:33]=[CH:34][C:25]2=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:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]1[N:31]=[CH:32][N:33]=[CH:34][C:25]2=1

참가 물질

6

반응물 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 81531DiisopropylethylamineHCID 690431204-methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)aniline

생성물 1

HCID 59774725N-[4-Methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)phenyl]-N'-[3-(trifluoromethyl)-phenyl]urea

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To 1-isocyanato-3-(trifluoromethyl)benzene (9.8 μl, 0.070 mmol) was added a solution of 4-methyl-3-(9H-pyrimido[4,5-b]indol-6-yl)aniline (17.5 mg, 0.064 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 16 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 (17.1 mg, 46.6%). 1H NMR (300 MHz, DMSO): δ 13.1 (bs, 1H), 9.66 (s, 1H), 9.15 (s, 2H), 8.92 (s, 1H), 8.33 (s, 1H), 8.01 (s, 1H), 7.72 (d, 1H), 7.62 (dd, 1H), 7.4-7.6 (m, 3H), 7.2-7.4 (m, 3H), 2.21 (s, 3H). MS (EI) m/z=462 (M+H).

후처리

  1. customreaction, typically 16 hours
  2. custompurified by preparative LCMS
  3. customto recover the product as a TFA salt (17.1 mg, 46.6%)

출처 및 근거

ORD 기록
ord-c38b2953652d47b685573ba2f8d9f2d5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

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