Felbinac → HCID 58885281, compound

HRID 1766328Notes

Reaction equation

HRID 1766328 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH2:7]C(O)=O)=[CH:3][CH:2]=1.[Cl:17][C:18]1[C:23]2[N:24]=[C:25]([CH3:27])[S:26][C:22]=2[CH:21]=[CH:20][C:19]=1[NH2:28].C(N(CC)CC)C.S(Cl)(Cl)=[O:37]>C1COCC1>[Cl:17][C:18]1[C:23]2[N:24]=[C:25]([CH3:27])[S:26][C:22]=2[CH:21]=[CH:20][C:19]=1[NH:28][C:7]([C:4]1[CH:3]=[CH:2][C:1]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][CH:5]=1)=[O:37]

Participants

6

Reactant 4

HCID 3332FelbinacHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 112178574-Chloro-2-methylbenzo[d]thiazol-5-amine

Product 1

HCID 58885281HCID 58885281, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 4-biphenylacetic acid (160 mg, 0.76 mmol) in thionyl chloride (1 mL) then with 4-chloro-2-methyl-benzothiazol-5-ylamine (50 mg, 0.25 mmol) in presence of triethylamine (0.5 mL) in THF (2 mL) according to method B gave biphenyl-4-carboxylic acid (4-chloro-2-methyl-benzothiazol-5-yl)-amide (60 mg, 0.15 mmol, 60% yield) as a pink powder after purification by chromatography on silica gel (eluent: DCM).

Sources & evidence

ORD record
ord-6b187cddb5c14f57a8b227464ef3cf74
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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