Hydrochloric Acid → HCID 44224664, compound

HRID 2068610Notes

Reaction equation

HRID 2068610 reaction equation
[N:1]1([C:7]([C:9]2[CH:10]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)[S:12][CH:13]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[CH2:29]([N:31](CC)CC)C.CN.Cl>C(Cl)Cl.CN(C=O)C>[CH3:29][NH:31][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[S:12][CH:13]=[C:9]([C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])[CH:10]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58110284HCID 58110284, compound

Product 1

HCID 44224664HCID 44224664, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-[4-(Piperidine-1-carbonyl)-thiophen-2-yl]-benzoic acid was taken up in DCM (5 mL) and oxalyl chloride (0.099 mL, 3 eq.) added with a drop of DMF. The mixture was then stirred for 1 hour and then evaporated and the residue taken up in DCM (5 mL). Triethylamine (0.106 mL, 2 eq.) was added followed by methylamine.HCl (28 mg, 1.1 eq). The mixture was stirred for 2 hours and then evaporated and the residue purified by column chromatography (EtOAc/iso-hexane) to give the desired product (21.9 mg, 17%). LCMS m/z 329 [M+H]+ R.T.=2.47 min (Analytical Method 3).

Workup

  1. customevaporated
  2. stirringThe mixture was stirred for 2 hours
  3. customevaporated
  4. customthe residue purified by column chromatography (EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-f738994e041644b18b913af9cd42da5f
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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