Hydrochloric Acid → HCID 66636934, compound

HRID 1094776Notes

Reaction equation

HRID 1094776 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[C@H:16]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)[CH2:15][C@H:14]3[C@H:12]([CH2:13]3)[CH2:11]2)=[O:9])[C:5]([O:29][CH2:30][CH2:31][CH3:32])=[CH:4][CH:3]=1.[ClH:33]>C(Cl)Cl>[ClH:33].[CH3:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[C@H:16]([CH2:17][NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)[CH2:15][C@H:14]3[C@H:12]([CH2:13]3)[CH2:11]2)=[O:9])[C:5]([O:29][CH2:30][CH2:31][CH3:32])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46209506HCID 46209506, compound

Product 1

HCID 66636934HCID 66636934, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[((1S,4S,6S)-3-{[6-methyl-3-(propyloxy)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]-5-(trifluoromethyl)-2-pyridinamine (0.036 g) in DCM (1 ml) was added HCl (1 M in Et2O) (0.161 ml, 0.161 mmol) and stirred for 30 minutes. The solvents were removed under reduced pressure to give a yellowish solid, which was triturated with Et2O (3×1 ml). The solvent was removed by suction and the residue was dried under vacuum at 40° C. overnight to yield the title compound E1 (0.038 g) as white solid. HPLC (walk-up): rt=4.48 min MS: (ES/+) m/z: 449 (M+1−HCl). C23H27F3N4O2HCl requires 484. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.29-8.45 (m, 1 H), 7.77-7.89 (m, 1 H), 7.58-7.66 (m, 2 H), 7.33-7.42 (m, 1 H), 6.85-7.04 (m, 1 H), 4.13-4.21 (m, 1 H), 3.95-4.02 (m, 2 H), 3.37-3.70 (m, 3 H), 2.60-2.74 (m, 1 H), 2.38-2.48 (m, 4 H), 1.56-1.73 (m, 2 H), 1.02-1.32 (m, 2 H), 0.82-0.96 (m, 4 H), 0.64-0.73 (m, 1 H), 0.20-0.28 (m, 1 H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customto give a yellowish solid, which
  3. customwas triturated with Et2O (3×1 ml)
  4. customThe solvent was removed by suction
  5. customthe residue was dried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-43dbde207a674c19b6b2f64252593e78
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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