Triethylamine → HCID 118092703, compound

HRID 2207364Notes

Reaction equation

HRID 2207364 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]=[C:10]=[O:11].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:19]=[C:20]([NH2:35])[CH:21]=[C:22]([NH:24][C:25]3[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=3)[CH:23]=2)[CH:13]=1>C1COCC1>[CH3:8][NH:9][C:10]([NH:35][C:20]1[CH:21]=[C:22]([NH:24][C:25]2[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=2)[CH:23]=[C:18]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH:19]=1)=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 118093083HCID 118093083, compound

Product 1

HCID 118092703HCID 118092703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Triethylamine (44.2 μL, 0.317 mmol) followed by methyl isocyanate (18.1 mg, 0.317 mmol was added to a solution of 5-(pyridin-3-yl)-N-[4-(trifluoromethyl)pyrimidin-2-yl]benzene-1,3-diamine (35 mg, 0.106 mmol) in THF (264 μL). The reaction mixture was heated to 40° C. for 4 hours, then cooled to room temperature and concentrated under reduced pressure. The solid was diluted with diethyl ether (5.00 mL) and was filtered to isolate 1-methyl-3-[3-(pyridin-3-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]urea as a tan powder. The product was further dried under reduced pressure. MS APC calc'd for C18H16F3N6O [M+H]+ 389. found 389. 1H NMR (500 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.81 (s, 1H), 8.75 (s, 1H), 8.63 (s, 1H), 8.56 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.70 (s, 1H), 7.63 (s, 1H), 7.55 (s, 1H), 7.49 (s, 1H), 7.26 (s, 1H), 6.06 (s, 1H), 2.64 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe solid was diluted with diethyl ether (5.00 mL)
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-59b560f0f667488198f7189d56387437
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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