Trifluoroacetic acid → Trifluoroacetic acid

HRID 1045352Notes

Reaction equation

HRID 1045352 reaction equation
[CH:1]1([CH2:4][C:5]2([C:17]([N:19]3[CH2:28][CH2:27][C:26]4[N:25]=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][C:21]=4[CH2:20]3)=[O:18])[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]2)[CH2:3][CH2:2]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[CH:1]1([CH2:4][C:5]2([C:17]([N:19]3[CH2:28][CH2:27][C:26]4[N:25]=[CH:24][C:23]([C:29]([F:30])([F:31])[F:32])=[CH:22][C:21]=4[CH2:20]3)=[O:18])[CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:3][CH2:2]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59569572HCID 59569572, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 59569569HCID 59569569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure D described in connection with Scheme 5. tert-Butyl 3-(cyclopropylmethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidine-1-carboxylate was dissolved in 8 mL of CH2Cl2 and 2 mL of TFA was then added to the solution at RT. The reaction mixture was stirred for 4 h and the solvent was evaporated. The desired product was obtained as TFA salt without further application for next step. 1H NMR (400 MHz, CDCl3): δ 8.78 (s, 1H), 7.82-7.78 (m, 1H), 6.86 (br s, 1H), 4.88 (dd, 2H), 3.98 (m, 3H), 3.42 (d, 1H), 3.33 (m, 1H), 3.22 (br s, 2H), 2.63 (m, 1H), 2.20 (m, 1H), 2.01-1.73 (m, 3H), 0.68 (s, 1H), 0.53 (br s, 2H), 0.066 (m, 2H); MS (ESI) m/z: Calculated for C18H22F3N3O: 353.2. found 354.1 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54c931a157c143eea0ed78e1056d82bf
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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