Hydrochloric Acid → HCID 66698067, compound

HRID 1619769Notes

Reaction equation

HRID 1619769 reaction equation
[F:1][CH:2]([F:37])[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](N3CCNCC3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[C:5]=2[N:4]=1.[CH3:38][S:39]([Cl:42])(=[O:41])=[O:40].[C:43]([O-:46])([O-])=O.[K+].[K+].Cl>C(Cl)Cl.CO.C(Cl)Cl.CCOC(C)=O>[ClH:42].[F:1][CH:2]([F:37])[C:3]1[N:7]([C:8]2[N:9]=[C:10]([O:46][CH:43]3[CH2:6][CH2:5][N:4]([S:39]([CH3:38])(=[O:41])=[O:40])[CH2:3][CH2:2]3)[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:13]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH2:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[C:5]=2[N:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66698096HCID 66698096, compound

Product 1

HCID 66698067HCID 66698067, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Reaction of N-[3-({2-(difluoromethyl)-1-[4-(4-morpholinyl)-6-(1-piperazinyl)-1,3,5-triazin-2-yl]-1H-benzimidazol-4-yl}oxy)propyl]-N,N-dimethylamine from the previous step with methanesulphonyl chloride and powdered K2CO3 in CH2Cl2, followed by chromatography on alumina eluting with CH2Cl2/EtOAc (1:1) g, and acidification with HCl in MeOH gave N-[3-({2-(difluoromethyl)-1-[4-{[1-(methylsulfonyl)-4-piperidinyl]oxy}-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazol-4-yl}oxy)propyl]-N,N-dimethylamine hydrochloride in 71% yield: 1H NMR (DMSO-d6) δ 10.07 (br s, exchangeable with D2O, 1H), 7.99 (d, J=8.2 Hz, 1H), 7.73 (t, JHF=52.7 Hz, 1H), 7.46 (t, J=8.2 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 5.27-5.21 (m, 1H), 4.34 (t, J=6.1 Hz, 2H), 3.86-3.85 (m, 4H), 3.74-3.71 (m, 4H), 3.44-3.38 (m, 2H), 3.20-3.14 2.93 (s, 3H), 2.82 (s, 6H), (m 2H), 2.28-2.26 (m, 2H), 2.15-2.10 (m, 2H); Anal. Calcd. for C26H29ClF2N8O5S.0.75H2O: C, 47.3; H, 5.9; Cl, 5.4; N, 17.0. Found: C, 47.3; H, 5.8; Cl, 5.4; N, 17.0%.

Sources & evidence

ORD record
ord-78e9cf97633e4e60a71df2bd5ff8207d
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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