Methanesulfonyl chloride → HCID 46917499, compound

HRID 1619765Notes

Reaction equation

[F:1][CH:2]([F:34])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([N:20]([CH3:27])[CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:5]=2[N:4]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>>[F:34][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([N:20]([CH3:27])[CH:21]3[CH2:26][CH2:25][N:24]([S:36]([CH3:35])(=[O:38])=[O:37])[CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:5]=2[N:4]=1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 66698073HCID 66698073, compound

Product 1

HCID 46917499HCID 46917499, compoundYield 56%

Procedure

Reaction of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(4-piperidinyl)-1,3,5-triazin-2-amine from the previous step with methanesulphonyl chloride as in Example 4 gave 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-N-[1-(methylsulfonyl)-4-piperidinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-amine in 56% yield: mp (CH2Cl2/MeOH) 190-192° C.; 1H NMR (DMSO-d6) (rotamers) δ 7.97 and 7.89 (2d, J=8.3, 8.5 Hz, 1H), 7.69 and 7.74 (2t, JHF=52.9 Hz, 1H), 7.46-7.39 (m, 1H), 6.95 (d, J=7.8 Hz, 1H), 4.69-4.61 (m, 1H), 3.98 (s, 3H), 3.80-3.69 (m, 10H), 3.09 and 2.95 (2s, 3H), 2.93-2.92 (2s, 3H), 2.92-2.78 (m, 2H), 1.93-1.67 (m, 4H); Anal. Calcd. for C23H30F2N8O4S: C, 50.0, H, 5.5; N, 20.3. Found: C, 49.5, H, 5.3; N, 20.0%.

Sources & evidence

ORD record: ord-59a8b112fc3e464e9573e45169dc6d14
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772287B2

Reaction notes

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