2-Fluorobenzoic acid → HCID 117704012, compound

HRID 1049870Notes

Reaction equation

HRID 1049870 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:10]([N:13]2[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[I-].ClC1C=CC=C[N+]=1C.[F:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:19][C:16]1([F:20])[CH2:17][CH2:18][N:13]([S:10]([C:4]2[S:3][C:2]([NH:1][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=3[F:30])=[C:6]([C:7]([NH2:9])=[O:8])[CH:5]=2)(=[O:12])=[O:11])[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 99352-Fluorobenzoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 117703985HCID 117703985, compound

Product 1

HCID 117704012HCID 117704012, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-Amino-5-(4,4-difluoro-piperidine-1-sulfonyl)-thiophene-3-carboxylic acid amide (53 mg, 0.18 mmol), TEA (125 μL, 0.90 mmol), DMAP (7 mg, 0.054 mmol), 2-Chloro-1-methylpyridinium iodide (60 mg, 0.23 mmol) and 2-fluorobenzoic acid (33 mg, 0.23 mmol) in DCM is stirred at 80° C. overnight. The mixture is then diluted with DCM and washed with aqueous NaHCO3. The organic phase is isolated evaporated, and the residue is purified by preparative chromatography to yield the desired product.

Workup

  1. washwashed with aqueous NaHCO3
  2. customThe organic phase is isolated
  3. customevaporated
  4. customthe residue is purified by preparative chromatography

Sources & evidence

ORD record
ord-28eddfa377f34d0ab8e1dd3babac4025
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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