Trifluoroacetic acid → HCID 68886670, compound

HRID 857890Notes

Reaction equation

HRID 857890 reaction equation
C(OC(N1CCC(NC([N:16]2[CH2:21][CH2:20][N:19]3[C:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:23]([Cl:28])[C:24]([C:25](=[O:27])[NH2:26])=[C:18]3[CH2:17]2)=O)CC1)=O)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>ClCCl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[Cl:28][C:23]1[C:24]([C:25]([NH2:26])=[O:27])=[C:18]2[CH2:17][NH:16][CH2:21][CH2:20][N:19]2[C:22]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 587618254-[(8-carbamoyl-7-chloro-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carbonyl)amino]piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 68886670HCID 68886670, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-carbamoyl-7-chloro-6-phenyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (2.75 g, Reference Example 2) in dichloromethane (60 mL) was treated with trifluoroacetic acid (5.64 mL). After stirring at room temperature for a further 3 hours the reaction mixture was further treated with trifluoroacetic acid (0.5 mL) and then further stirred for 1 hour. The reaction mixture was evaporated to afford an oil, which was azeotroped with toluene and then triturated with diethyl ether to give the title compound (2.61 g) as a white solid, m.p. 205–208° C. [Elemental Analysis: C, 49.32; H, 3.88; N, 10.78%. Calculated for C16H15ClF3N3O3: C, 49.30; H, 3.88; N, 10.78%].

Workup

  1. stirringfurther stirred for 1 hour
  2. customThe reaction mixture was evaporated
  3. customto afford an oil, which
  4. customwas azeotroped with toluene
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-fcad78ddd6334d0995f8720e4587706a
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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