Hydrochloric Acid → HCID 66698050, compound

HRID 1619802Notes

Reaction equation

HRID 1619802 reaction equation
[F:1][CH:2]([F:46])[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:30]3[CH2:35][CH2:34][CH2:33][N:32]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:31]3)[CH2:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:9]=2)[C:6]2[CH:40]=[CH:41][CH:42]=[C:43]([O:44][CH3:45])[C:5]=2[N:4]=1.[ClH:47]>CO>[ClH:47].[F:46][CH:2]([F:1])[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:30]3[CH2:35][CH2:34][CH2:33][N:32]([S:36]([CH3:39])(=[O:38])=[O:37])[CH2:31]3)[CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:9]=2)[C:6]2[CH:40]=[CH:41][CH:42]=[C:43]([O:44][CH3:45])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59506104HCID 59506104, compound

Product 1

HCID 66698050HCID 66698050, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[1-(methylsulfonyl)-3-piperidinyl]-6-(4-morpholinyl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine 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 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-[1-(methylsulfonyl)-3-piperidinyl]-6-(4-morpholinyl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine hydrochloride: mp (MeOH) 186-190° C.; 1H NMR (DMSO-d6) (rotamers) δ 10.65 and 10.43 (2br, 1H), 7.90 and 7.89 (2d, J=8.2, 8.1, Hz, 1H), 7.70 and 7.65 (2t, JHF=52.9, Hz, 1H), 7.46 and 7.39 (2t, J=8.3, 8.2 Hz, 1H), 6.96 (m, 1H), 4.75-4.66 and 4.51-4.44 (2m, 1H), 3.98 and 3.97 (2s, 3H), 3.98-3.59 (m, 16H), 3.46-3.24 (m, 2H), 3.18-2.85 (m, 5H), 2.92 (s, 3H), 2.73-2.67 (m, 1H), 2.09-1.89 (m, 6H); Anal. Calcd. for C29H42ClF2N9O5S.1.25H2O: C, 48.1; H, 6.2; N, 17.4; Cl, 4.9. Found: C, 47.9; H, 6.2; N, 17.3; Cl, 5.2%.

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-89641308340a47f9bc733becf9bbd11e
Source dataset
uspto-grants-2014_07
Patent number
US08772287B2

Reaction notes

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