Trifluoroacetic acid → HCID 90039950, compound

HRID 1485903Notes

Reaction equation

HRID 1485903 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1C(OC(C)(C)C)=O)=[O:11].[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>C(Cl)Cl>[F:32][C:31]([F:34])([F:33])[C:29]([OH:35])=[O:30].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]([C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][NH:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90040707HCID 90040707, compound

Product 1

HCID 90039950HCID 90039950, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(2,6-difluorophenylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (90 mg, 232 μmol, Eq: 1.00) in DCM (2 mL) was added TFA (2 mL, 26.0 mmol, Eq: 112) and the resulting solution stirred at RT for 1 h. The reaction mixture was concentrated in vacuo and the residue azeotroped with n-heptanes to give (S)—N-(2,6-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide trifluoroacetate which was used without purification (93 mg), m/z=289 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue azeotroped with n-heptanes

Sources & evidence

ORD record
ord-604377e8658f49d5a86d41816d4fcad8
Source dataset
uspto-grants-2016_08
Patent number
US09422332B2

Reaction notes

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