Hydrochloric Acid → HCID 67546111, compound

HRID 1619840Notes

Reaction equation

HRID 1619840 reaction equation
[F:1][CH:2]([F:39])[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]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[N:9]=2)[C:6]2[CH:33]=[CH:34][CH:35]=[C:36]([O:37][CH3:38])[C:5]=2[N:4]=1.[Cl:40][CH2:41][S:42](Cl)(=[O:44])=[O:43].C([O-])([O-])=O.[K+].[K+].Cl>C(Cl)Cl.CO>[ClH:40].[Cl:40][CH2:41][S:42]([N:30]1[CH2:31][CH2:32][CH:27]([N:20]([C:10]2[N:9]=[C:8]([N:7]3[C:6]4[CH:33]=[CH:34][CH:35]=[C:36]([O:37][CH3:38])[C:5]=4[N:4]=[C:3]3[CH:2]([F:1])[F:39])[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=2)[CH2:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[CH2:28][CH2:29]1)(=[O:44])=[O:43]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 77054(Chloromethyl)sulfonyl chlorideHCID 67544007HCID 67544007, compound

Product 1

HCID 67546111HCID 67546111, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Reaction of N1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-(4-piperidinyl)-1,3-propanediamine (Example 21) with chloromethanesulfonyl chloride and K2CO3 in CH2Cl2, followed by conversion to the hydrochloride salt with 1.25 M HCl in methanol gave N1-{1-[(chloromethyl)sulfonyl]-4-piperidinyl}-N1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-1,3-propanediamine hydrochloride in 44% yield: mp (MeOH) 222-225° C.; 1H NMR (DMSO-d6) δ 9.89 (br, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.71 (t, JHF=53.0 Hz, 1H), 7.47-7.41 (m, 1H), 7.00 (d, J=8.2 Hz, 1H), 5.17 and 5.11 (2s, 2H), 4.74-4.71 and 4.66-4.53 (2m, 1H), 3.98 (s, 3H), 3.92-3.82 (m, 6H), 3.71 (m, 4H), 3.60-3.51 (m, 2H), 3.16-3.04 (m, 4H), 2.75 and 2.70 (2s, 6H), 2.02-1.80 (m, 6H); Anal. Calcd. for C27H39Cl2F2N9O4S.0.5; H2O: C, 46.1; H, 5.7; N, 17.9; Cl, 10.1. Found: C, 46.1; H, 5.8; N, 17.9; Cl, 9.7%.

Sources & evidence

ORD record
ord-d9414ebe5050459ba0a8c0f22ab75da7
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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