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Dimethylformamide → 4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 1791370
Notes
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Reaction equation

HRID 1791370 reaction equation
CC(OC([CH:8]1[S:12][CH2:11][CH:10]([C:13]([OH:15])=O)[NH:9]1)=O)(C)C.[CH2:16](OC(Cl)=O)[CH:17]([CH3:19])[CH3:18].CN1CC[O:28]CC1.[C:31]([C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([NH:38]O)=[NH:37])#[N:32].CN([CH:46]=[O:47])C>C1COCC1>[C:17]([O:28][C:46]([N:9]1[C@@H:10]([C:13]2[O:15][N:38]=[C:36]([C:35]3[CH:40]=[CH:41][CH:42]=[C:33]([C:31]#[N:32])[CH:34]=3)[N:37]=2)[CH2:11][S:12][CH2:8]1)=[O:47])([CH3:19])([CH3:18])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 220327532-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-4-carboxylic acidHCID 178509779HCID 178509779, compound

Product 1

HCID 69619359
4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester
Yield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
120 °C

Procedure

4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(S)-thiazolidine-3-carboxylic acid tert-butyl ester (212 mg, 20%, yellow oil) was prepared according to the procedure in Example 25 from Boc-L-thiazolidine-4-carboxylic acid (696 mg, 2.98 mmol) with isobutylchloroformate (0.43 ml, 3.28 mmol) and N-methylmorpholine (0.36 ml, 3.28 mmol) in THF (5 ml) at 40° C. for 2 h. Then 3-cyano-N-hydroxy-benzamidine (577 mg, 3.58 mmol) and additional N-methylmorpholine (0.39 ml, 3.58 mmol) and THF (4 ml) at room temperature overnight followed by extraction of the product and addition of DMF (2 ml) and the mixture was heated at 120° C. overnight. The crude residue was purified on silica gel using 20% ethyl acetate.

Workup

  1. customThe crude residue was purified on silica gel using 20% ethyl acetate

Sources & evidence

ORD record
ord-b04a569322c9446191de98fea4a5dc0b
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074809B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes