2,4-Dichloro-6-morpholino-1,3,5-triazine → HCID 86645851, compound

HRID 516287Notes

Reaction equation

HRID 516287 reaction equation
[Si:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH:18]([F:20])[F:19])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:21][C:22]1[N:27]=[C:26](Cl)[N:25]=[C:24]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[N:23]=1>CC(C)=O>[Si:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH:18]([F:19])[F:20])[N:14]([C:26]3[N:27]=[C:22]([Cl:21])[N:23]=[C:24]([N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)[N:25]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 23082131HCID 23082131, compound

Product 1

HCID 86645851HCID 86645851, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Reaction of 4-(tert-butyldimethylsilyloxy)-2-(difluoromethyl)-1H-benzimidazole with 2,4-dichloro-6-(4-morpholinyl)-1,3,5-triazine as in Example 2, but using acetone as solvent, followed by chromatography on silica gel eluting with CH2Cl2/hexanes 3:1 gave 4-(tert-butyldimethylsilyloxy)-1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole: mp (hexanes) 143-145° C.; 1H NMR (CDCl3) δ 7.99 (d, J=8.4 Hz, 1H), 7.46 (t, JHF=53.5 Hz, 1H), 7.32 (t, J=8.2 Hz, 1H), 6.88 (d, J=8.0 Hz, 1H), 3.96 (m, 3.5H), 3.88 (m, 0.5H), 3.81 (m, 3.5H), 3.75 (m, 0.5H), 1.05 (s, 9H), 0.29 (s, 6H); MS (APCI+) 497.9/499.9 MH+. Anal. Calcd. for C21H27ClF2N6O2Si: C, 50.75; H, 5.5; N, 16.9. Found: C, 50.7; H, 5.6; N, 17.0%.

Sources & evidence

ORD record
ord-ce8aba044d2a40b0a382a7bea6c9245d
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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