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Diisopropylethylamine → 3-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

HRID 2237641
Notes
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Reaction equation

HRID 2237641 reaction equation
Cl.Cl.[CH2:3]([O:5][C:6]([C:8]1[O:12][N:11]=[C:10]([CH2:13][NH2:14])[N:9]=1)=[O:7])[CH3:4].C(N(C(C)C)C(C)C)C.[Cl:24][C:25]1[S:29][C:28]([C:30](O)=[O:31])=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>[CH2:3]([O:5][C:6]([C:8]1[O:12][N:11]=[C:10]([CH2:13][NH:14][C:30]([C:28]2[S:29][C:25]([Cl:24])=[CH:26][CH:27]=2)=[O:31])[N:9]=1)=[O:7])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 686910763-Aminomethyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester dihydrochloride

Product 1

HCID 593029563-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl esterYield 81.6%

Reagents, catalysts & solvents 3

HCID 151348
Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate
Catalyst
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-aminomethyl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester dihydrochloride (555 mg) at r.t. in DMF (10 ml) under an argon atmosphere were added N-ethyldiisopropylamine (1.82 ml), 5-chloro-2-thiophenecarboxylic acid (565 mg) and BOP (1.54 mg). The mixture was stirred over night, then diluted with EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1) to give 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (586 mg) as off-white solid. MS 316.0 ([M+H]+)

Workup

  1. washwashed with H2O
  2. extractionThe aqueous phase was back extracted with EtOAc and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane->cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-ec9db8cc7b674cec8394dbecdebe97ee
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07718679B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes