Trifluoroacetic acid → HCID 22110953, compound

HRID 565398Notes

Reaction equation

HRID 565398 reaction equation
FC(F)(F)C(O)=O.CC(OC([N:15]1[CH:24]([C:25]([N:27]2[CH2:31][CH2:30][CH2:29][CH:28]2[C:32]#[N:33])=[O:26])[CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:36][CH3:37])=[C:20]([O:34][CH3:35])[CH:21]=2)[CH2:16]1)=O)(C)C>C(#N)C>[CH3:35][O:34][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:36][CH3:37])[CH2:16][NH:15][CH:24]([C:25]([N:27]1[CH2:31][CH2:30][CH2:29][CH:28]1[C:32]#[N:33])=[O:26])[CH2:23]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70248420HCID 70248420, compound

Product 1

HCID 22110953HCID 22110953, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoroacetic acid (1.2 mL, 15.6 mmol) was added to a solution of the title A compound, 3-(2-cyano-1-pyrrolidinyl)carbonyl-3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 1,1-dimethylethyl ester [Diastereomer B] (196 mg, 0.47 mmol) in acetonitrile (9 mL) at room temperature overnight. The mixture was then concentrated under vacuum. The residue was taken up in another portion of acetonitrile (8 mL) and concentrated again under vacuum. The brown oily residue was triturated with ether to form a solid which was collected and washed with ether and dried under vacuum to give 157 mg (78%) of the title compound as a yellow solid, 88% pure by HPLC, m.p. 153-154° C. (dec). 1H NMR (CD3OD, 300 MHz): 6.85 (s, 1H), 6.8 (s, 1H), 4.85 (dd, 1H), 4.55 (dd, 1H), 4.35 (2, 2H), 3.8 (s, 6H), 3.6-3.8 (m, 2H), 3.4 (dd, 1H), 3.1 (dd, 1H), 2.1-2.4 (m, 4H). MS: 316 (MH+ for free amine).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. concentrationconcentrated again under vacuum
  3. customThe brown oily residue was triturated with ether
  4. customto form a solid which
  5. customwas collected
  6. washwashed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-26a68df9c9a64124beb794a9abc45f22
Source dataset
uspto-grants-2001_01
Patent number
US06172081B2

Reaction notes

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