Hydrochloric Acid → HCID 86700764, compound

HRID 1256494Notes

Reaction equation

HRID 1256494 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][N:30]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:29][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[CH2:28][CH2:29][N:30]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:31][CH2:32]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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46917726HCID 46917726, compound

Product 1

HCID 86700764HCID 86700764, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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)-4-piperidinyl]-1,3-propanediamine from the previous step in MeOH (20 mL) was treated with a slight excess of 1.25 M HCl in MeOH (1.1 equiv.) 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)-4-piperidinyl]-1,3-propanediamine hydrochloride: mp (CH2Cl2/MeOH) 241-243° C.; 1H NMR (DMSO-d6) (rotamers) δ 9.95 (br, 1H), 7.90 and 7.89 (2d, J=8.2, 8.3 Hz, 1H), 7.71 and 7.70 (2t, JHF=52.9, 53.0 Hz, 1H), 7.45 (t, J=8.2 Hz, 1H), 6.96 (d, J=8.1 Hz, 1H), 4.69-4.55 (m, 1H), 3.98 (s, 3H), 3.82-3.70 (m, 10H), 3.60-3.52 (m, 2H), 3.12-3.05 (m, 2H), 2.94 and 2.92 (2s, 3H), 2.90-2.79 (m, 2H), 2.74 and 2.70 (2s, 6H), 2.02-1.80 (m, 6H); Anal Calcd. for C27H39F2N9O4S.1.25HCl.0.5H2O: C, 47.8; H, 6.1; Cl, 6.5; N, 18.6. Found: C, 47.9; H, 6.0; Cl, 6.4; N, 18.6%.

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-d21fbb4a76cc4a509a088a2a02cd3dd2
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

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