Hydrochloric Acid → HCID 67546111, compound

Participants

Reaction Steps

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) δ9.89 (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.0.5H2O: 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%.

Provenance & Evidence