Potassium Carbonate → HCID 46918270, compound

HRID 1619844Notes

Reaction equation

HRID 1619844 reaction equation
[F:1][CH:2]([F:33])[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[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:5]=2[N:4]=1.[Cl:34][CH2:35][S:36](Cl)(=[O:38])=[O:37].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:34][CH2:35][S:36]([NH:26][CH:23]1[CH2:24][CH2:25][N:20]([C:10]2[N:9]=[C:8]([N:7]3[C:6]4[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:5]=4[N:4]=[C:3]3[CH:2]([F:1])[F:33])[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=2)[CH2:21][CH2:22]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77054(Chloromethyl)sulfonyl chlorideHCID 66698054HCID 66698054, compound

Product 1

HCID 46918270HCID 46918270, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-4-piperidinamine (Example 17) with chloromethanesulfonyl chloride and K2CO3 in CH2Cl2 gave chloro-N-{1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-4-piperidinyl}methanesulfonamide in 56% yield: mp (CH2Cl2/MeOH) 230-232° C.; 1H NMR (DMSO-d6) δ 7.88 (d, J=8.0 Hz, 1H), 7.87 (br, 1H), 7.69 (t, JHF=52.9 Hz, 1H), 7.41 (t, J=8.2 Hz, 1H), 6.95 (d, J=7.9 Hz, 1H), 4.95 (s, 2H), 4.59-4.49 (m, 2H), 3.98 (s, 3H), 3.81-3.79 (m, 4H), 3.70-3.69 (m, 4H), 3.55 (br, 1H), 3.22-3.12 (m, 2H), 1.96 (br, 2H), 1.46-1.41 (m, 2H); Anal. Calcd. for C22H27ClF2N8O4S: C, 46.1; H, 4.75; N, 19.6. Found: C, 46.4; H, 4.8; N, 19.6%

Sources & evidence

ORD record
ord-33fa4e92effa4504a730391ee23da085
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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