Methanesulfonyl chloride → HCID 46917869, compound

HRID 516352Notes

Reaction equation

[F:1][CH:2]([F:31])[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]3[CH2:23][CH:22]([NH2:24])[CH2:21]3)[N:9]=2)[C:6]2[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:5]=2[N:4]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>>[F:31][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]3[CH2:21][CH:22]([NH:24][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:23]3)[N:9]=2)[C:6]2[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:5]=2[N:4]=1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 66698112HCID 66698112, compound

Product 1

HCID 46917869HCID 46917869, compoundYield 86%

Procedure

Reaction of 1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-3-azetidinamine and methanesulfonyl chloride as in Example 28 gave N-{1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-3-azetidinyl}methanesulfonamide in 86% yield: mp 307-309° C.; 1H NMR (DMSO-d6) δ7.98 (d, J=8.1 Hz, 1H), 7.92 (br s, 1H), 7.73 (t, JHF=53.0 Hz, 1H), 7.40 (t, J=8.2 Hz, 1H), 6.95 (d, J=7.7 Hz, 1H), 4.54-4.33 (m, 3H), 4.07-3.97 (m, 2H), 3.97 (s, 3H), 3.80-3.78 (m, 4H), 3.69 (m, 4H), 2.97 (s, 3H); Anal. Calcd. for C20H24F2N8O4S.0.25H2O: C, 46.6; H, 4.8; N, 21.8. Found: C, 46.7; H, 4.8; N, 22.0%.

Sources & evidence

ORD record: ord-68fc9b6013574533811357ff8a47812c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108980B2

Reaction notes

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