Dimethylformamide → (5R,6S,8S)-5-Methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-amine

HRID 2179468Notes

Reaction equation

HRID 2179468 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[N:10]2[C:21]([CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:22][N:23]=[C:9]12)(C)(C)C.FC(F)(F)C(O)=O.CN(C)C=O>ClCCl>[CH3:20][C@H:11]1[N:10]2[C:21]([CH2:24][C:25]([F:27])([F:26])[F:28])=[CH:22][N:23]=[C:9]2[C@@H:8]([NH2:7])[CH2:13][C@H:12]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 131733072tert-Butyl[(5R,6S,8S)-5-methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate

Product 1

HCID 118185005(5R,6S,8S)-5-Methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-amineYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[(5R,6S,8S)-5-methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate (18.4 mg, 0.045 mmol) in dichloromethane (900 μL) was added trifluoroacetic acid (104 μL, 1.35 mmol). The mixture was stirred 90 min. N,N-dimethylformamide was added and the dichloromethane was removed under vacuum. The resulting mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid). Product containing fractions were treated with 1 M hydrochloric acid and concentrated to give the hydrochloride salt of the title compound (10.3 mg). MS 310.3 (M+1).

Workup

  1. customthe dichloromethane was removed under vacuum
  2. customThe resulting mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)
  3. additionProduct containing fractions
  4. additionwere treated with 1 M hydrochloric acid
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3987be7261d04378abdb5a24a1b60759
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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