Potassium Carbonate → tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate

HRID 1619773Notes

Reaction equation

HRID 1619773 reaction equation
[F:1][CH:2]([F:22])[C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[C:11]([O:12][CH3:13])[C:5]=2[N:4]=1.[Cl:23][C:24]1[N:29]=[C:28](Cl)[N:27]=[C:26]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:23][C:24]1[N:25]=[C:26]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[N:27]=[C:28]([N:7]2[C:6]3[CH:8]=[C:9]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:10]=[C:11]([O:12][CH3:13])[C:5]=3[N:4]=[C:3]2[CH:2]([F:1])[F:22])[N:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 66698048tert-butyl 2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate

Product 1

HCID 86645852tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamateYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate (0.47 g, 1.5 mmol), 2,4-dichloro-6-(4-morpholinyl)-1,3,5-triazine (0.35 g, 1.5 mmol), and powdered K2CO3 (0.83 g, 6 mmol) in DMF (10 mL) was stirred at room temperature for 30 min. The reaction mixture was then diluted with water. The resulting precipitate was collected, washed with water and then MeOH, and dried to give 0.45 g (59% yield) of tert-butyl 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazol-6-yl-carbamate: mp (CH2Cl2/MeOH)>300° C.; 1H NMR (CDCl3) δ 8.45 (d, J=0.6 Hz, 1H), 7.57 (t, JHF=53.6 Hz, 1H), 6.67 (br, exchangeable with D2O, 1H), 6.63 (d, J=0.9 Hz, 1H), 4.11 (m, 2H), 4.02 (s, 3H), 3.97 (m, 2H), 3.88 (m, 2H), 3.82 (m, 2H), 1.52 (s, 9H); Anal. Calcd. for C21H24ClF2N7O4: C, 49.3; H, 4.7; N, 19.15. Found: C, 49.4; H, 4.8; N, 19.2%.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. dry with materialMeOH, and dried

Sources & evidence

ORD record
ord-d9066ab10eb644bf868c12e94d35c5f5
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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