Triethylamine → HCID 58761882, compound

HRID 857884Notes

Reaction equation

HRID 857884 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([C:18]([NH2:20])=[O:19])=[C:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[CH:17]=1.C(N(CC)CC)C.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[S:38][C:37]([S:39](Cl)(=[O:41])=[O:40])=[CH:36][CH:35]=1>C(#N)C>[Cl:8][C:9]1[C:10]([C:18]([NH2:20])=[O:19])=[C:11]2[CH2:16][N:15]([S:39]([C:37]3[S:38][C:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=4)=[CH:35][CH:36]=3)(=[O:40])=[O:41])[CH2:14][CH2:13][N:12]2[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chlorideHCID 68889373HCID 68889373, compound

Product 1

HCID 58761882HCID 58761882, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 7-chloro-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (156 mg, Reference Example 24) in dry acetonitrile (13 mL) was treated with dry triethylamine (0.28 mL), then with 5-(pyrid-2-yl)thiophene-2-sulfonyl chloride (127 mg). After stirring at 60° C. for 4 hours the reaction mixture was allowed to cool to room temperature and evaporated. The residue was subjected to column chromatography on silica eluting with ethyl acetate to give 7-chloro-2-(5-pyridin-2-ylthiophene-2-sulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (51 mg) as a white solid, m.p. 213–214° C. [Elemental analysis: C, 47.99; H, 3.44; N, 12.97%; Calculated for C17H15ClN4O3S2: C, 48.28; H, 3.58; N, 13.25%].

Workup

  1. temperatureto cool to room temperature
  2. customevaporated

Sources & evidence

ORD record
ord-4af6af0c78674b008479283af941547f
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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