Ethyl Acetate → HCID 58342000, compound

HRID 339536Notes

Reaction equation

HRID 339536 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23]C)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br.CCCCCC.CCOC(C)=O.CCOC(C)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 21226206Ethyl acetate hexaneHCID 67312575HCID 67312575, compound

Product 1

HCID 58342000HCID 58342000, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared as described in the Demethylation section using 3-amino-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide (50 mg, 0.13 mmol) in dry DCM (3 ml) and BBr3 (1.0 M solution in DCM, 0.67 ml, 0.67 mmol) to give the title compound (29 mg, 60%) as a pale brown solid after work-up and flash chromatography (1:1 Hexane/EtOAc followed by EtOAc).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-13920af3b5eb490c921d8d99b190909a
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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