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

HRID 77709

反応式

HRID 77709 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c38b2953652d47b685573ba2f8d9f2d5
出典データセット
uspto-grants-2014_09
特許番号
US08841318B2

関連ノート

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