Hydrochloric Acid → HCID 67544540, compound

HRID 516330Notes

Reaction equation

HRID 516330 reaction equation
[F:1][CH:2]([F:43])[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][CH2:30][N:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28]3)[CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[N:9]=2)[C:6]2[CH:37]=[CH:38][CH:39]=[C:40]([O:41][CH3:42])[C:5]=2[N:4]=1.[ClH:44]>CO>[ClH:44].[F:43][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]([CH:27]3[CH2:32][CH2:31][CH2:30][N:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:28]3)[CH2:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])[N:9]=2)[C:6]2[CH:37]=[CH:38][CH:39]=[C:40]([O:41][CH3:42])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46917725HCID 46917725, compound

Product 1

HCID 67544540HCID 67544540, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of N1-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-[1-(methylsulfonyl)-3-piperidinyl]-1,3-propanediamine from the previous step in MeOH (20 mL) was added a slight excess of 1.25 M HCl in MeOH (0.18 mL) to give a clear solution. The solvent was removed under vacuum and the residue was washed with EtOAc to give N1-[4-[2-(Difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-N3,N3-dimethyl-N1-[1-(methylsulfonyl)-3-piperidinyl]-1,3-propanediamine hydrochloride: mp (MeOH/EtOAc/hexanes) 189° C. (dec.); 1H NMR (DMSO-d6) (rotamers) δ 10.11 and 9.98 (2br, 1H), 7.89 (d, J=8.4 Hz, 1H), 7.71 and 7.65 (2t, JHF=52.8, 52.9 Hz, 1H), 7.45 and 7.38 (2t, J=8.2, 1H), 6.97 and 6.95 (2d, J=5.7, 5.8 Hz, 1H), 4.73-4.65 and 4.51-4.44 (2m, 1H), 3.97 and 3.96 (2s, 3H), 3.91-3.57 (m, 12H), 3.11-3.03 (m, 2H), 2.93 and 2.92 (2s, 6H), 2.95-2.82 (m, 1H), 2.76-2.66 (m, 6H), 2.05-1.85 (m, 4H); Anal. Calcd. for C27H38N9O4. 1.25HCl.0.5H2O: C, 47.8; H, 6.1; Cl, 6.5; N, 18.6. Found: C, 47.6; H, 6.1; Cl, 6.6%; N, 17.8%.

Workup

  1. customto give a clear solution
  2. customThe solvent was removed under vacuum
  3. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-c18d02364e5342429271484bd0f9e30f
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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