Triethylamine → 7-Chloro-2-(3-cyclohexylpropionyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo [1,2-a]pyrazine-8-carboxylic acid amide

HRID 857881Notes

Reaction equation

HRID 857881 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[CH:34]1([CH2:40][CH2:41][C:42](Cl)=[O:43])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>ClCCl>[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][N:15]([C:42](=[O:43])[CH2:41][CH2:40][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734098Cyclohexylpropionyl chlorideHCID 68886670HCID 68886670, compound

Product 1

HCID 587619987-Chloro-2-(3-cyclohexylpropionyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo [1,2-a]pyrazine-8-carboxylic acid amideYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (100 mg, Reference Example 1) in dry dichloromethane (10 mL) was treated with dry triethylamine (0.11 mL), then with a solution of 3-cyclohexylpropionyl chloride (45 mg) in dry dichloromethane (5 mL). After stirring at room temperature overnight the reaction mixture was washed with water, then the organic phase was dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of methanol and dichloromethane (1:19, v/v) to give 7-chloro-2-(3-cyclohexylpropionyl)-6-phenyl-1,2,3,4-tetrahydropyrrolo [1,2-a]pyrazine-8-carboxylic acid amide (80 mg) as a white solid, m.p. 181–182° C. MS: 416 [MH]+, 414 [MH]+.

Workup

  1. washwas washed with water
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customevaporated
  4. additionThe residue was subjected to column chromatography on silica eluting with a mixture of methanol and dichloromethane (1:19

Sources & evidence

ORD record
ord-3c52f0fd4b27404aaf37107b1a3ee640
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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