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

HRID 1894881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894881
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4d8c31f024104dd69c7910f6d904010b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513270B2

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