Formic Acid → HCID 11153785, compound

HRID 1593522Notes

Reaction equation

HRID 1593522 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].CC([O-])(C)C.[K+].C(O)=O>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:21](=[O:22])[C:20]1[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=1[Cl:18]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 691102-Chlorobenzoyl chlorideHCID 234666Benzothiazol-2-yl-(4-chloro-phenyl)-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 11153785HCID 11153785, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 39.1 mg (0.15 mmol) Benzothiazol-2-yl-(4-chloro-phenyl)-amine in 0.5 ml THF, 45.2 mg (0.18 mmol) 2-chlorobenzoyl chloride in 0.18 ml THF and 0.17 ml of a 1 M solution of KOtBu in THF was heated to 50° C. for 16 h. After addition of 0.5 ml formic acid the mixtures are subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of the product fractions yielded 40.1 mg (67%) of the title compound. MS (m/e): 399.3 (MH+, 100%).

Workup

  1. customHPLC separation on reversed phase
  2. washeluting with an acetonitrile/water gradient
  3. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-6a995aa347864c6486a97d592835b4e6
Source dataset
uspto-grants-2007_11
Patent number
US07297707B2

Reaction notes

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