Dimethylformamide → HCID 178501266, compound

HRID 1035715Notes

Reaction equation

HRID 1035715 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=[O:4].C(N(C(C)C)CC)(C)C.[Cl:30][C:31]1[CH:32]=[C:33]([C:37]2[S:41][C:40]([NH2:42])=[N:39][N:38]=2)[CH:34]=[CH:35][CH:36]=1.CN(C=O)C>ClCCl.O>[Cl:30][C:31]1[CH:32]=[C:33]([C:37]2[S:41][C:40]([NH:42][C:16]([C:15]3[CH:14]=[CH:13][C:12]([O:11][C@@H:8]4[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]4)=[CH:20][CH:19]=3)=[O:18])=[N:39][N:38]=2)[CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27723065-(3-Chlorophenyl)-1,3,4-thiadiazol-2-amineHCID 178501272HCID 178501272, compound

Product 1

HCID 178501266HCID 178501266, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.351 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (1.26 mmol, 1 eq.) is placed in 5 mL of dichloromethane at room temperature. 0.42 mL of diisopropylethylamine (2.52 mmol, 2 eq.), 0.705 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (1.51 mmol, 1.2 eq.) and 0.267 g of 3-chlorophenyl-1,3,4-thiadiazol-2-amine (1.26 mmol, 1 eq.) are added successively. 2 mL of DMF are added. The reaction mixture is stirred for 1 day at room temperature, diluted in dichloromethane, and water is added. Filtration of this medium gives 0.06 g of methyl cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate. The organic phase is separated out by settling, washed with water, dried over sodium sulfate, filtered and evaporated. The residue is taken up in ethanol, filtered off by suction and washed with diethyl ether. 0.090 g of methyl cis-4-{4-[5-(3-chlorophenyl)[1.3.4]thiadiazol-2-ylcarbamoyl]phenoxy}cyclohexanecarboxylate is obtained.

Workup

  1. filtrationFiltration of this medium

Sources & evidence

ORD record
ord-b73a4786297b475b8eed74b75d126587
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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