Hydrochloric Acid → HCID 46869363, compound

HRID 1628328Notes

Reaction equation

HRID 1628328 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][CH2:12][N:13]3[C:16](=[O:33])[C@@H:17]([NH:25]C(=O)OC(C)(C)C)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1.C(O)(C(F)(F)F)=O.[ClH:41]>ClCCl.CCOCC>[ClH:41].[NH2:25][C@@H:17]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:15]=2)[CH2:11][CH2:12]1)=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69620982HCID 69620982, compound

Product 1

HCID 46869363HCID 46869363, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (S)-1-(6-(1-methyl-1H-pyrazol-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (60.0 mg, 134 μmol) was dissolved in dichloromethane (1.5 mL) and TFA (1.50 mL, 19 mmol) was added and the solution was stirred for three hours. The reaction mixture was then concentrated to dryness and then taken up in ethyl acetate and extracted and basified with saturated sodium bicarbonate solution. The organic layer was then concentrated and the residue was dissolved in ethyl acetate and 3.0 equivalents of 1M HCl in ether solution was added forming an off-white precipitate that was filtered and washed with hexanes to give (2S)-2-amino-1-(6-(1-methyl-1H-pyrazol-4-yl)indolin-1-yl)-3-phenylpropan-1-one hydrochloride 82. MS ESI (pos.) m/e: 347.2 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. extractionextracted
  3. concentrationThe organic layer was then concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customforming an off-white precipitate that
  6. filtrationwas filtered
  7. washwashed with hexanes

Sources & evidence

ORD record
ord-968ac73ef7524f56af7705f57036eaf3
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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