Triethylamine → HCID 59318032, compound

HRID 2190651Notes

Reaction equation

HRID 2190651 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18](=[O:31])[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.[C:32]1(=[O:42])[C:36]2([CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:35][C:34](=[O:41])[O:33]1.C(N(CC)CC)C>CN(C=O)C>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:17][C:18]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([C:34](=[O:41])[CH2:35][C:36]3([C:32]([OH:42])=[O:33])[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:29][CH2:30]2)=[CH:21][CH:20]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27371022-oxaspiro[4.4]nonane-1,3-dioneHCID 86641509HCID 86641509, compound

Product 1

HCID 59318032HCID 59318032, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-benzothiazol-2-yl-4-piperazin-1-yl-benzamide trifluoroacetate (40 mg) was mixed with 2-oxa-spiro[4,4]nonane-1,3-dione (30 mg) in DMF (5 mL) containing triethylamine (0.1 mL) and the mixture was stirred foe 5 hrs. Solvents were evaporated and the residue was treated with ethyl acetate and hydrochloric acid solution (0.1N). The precipitate from the organic layer was filtered to give 1-(2-{4-[4-(benzothiazol-2-ylcarbamoyl)-phenyl]-piperazin-1-yl}-2-oxo-ethyl)-cyclopentanecarboxylic acid as a white solid (30 mg). LCMS calc for C26H28N4O4S (m/e) 492, obsd 493.

Workup

  1. customSolvents were evaporated
  2. additionthe residue was treated with ethyl acetate and hydrochloric acid solution (0.1N)
  3. filtrationThe precipitate from the organic layer was filtered

Sources & evidence

ORD record
ord-dad6f38bcd174ab0b0565e86c9c4b828
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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