Cyanogen Bromide → HCID 90047746, compound

HRID 1754260Notes

Reaction equation

HRID 1754260 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]3[N:11]=[C:12]([CH2:14][C:15]([NH:17][NH2:18])=[O:16])[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[K+].[N:26]#[C:27]Br>CO>[C:1]1([C:7]2[CH:20]=[CH:19][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:16][C:27]([NH2:26])=[N:18][N:17]=4)[S:13][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516893Potassium BicarbonateHCID 58470188HCID 58470188, compound

Product 1

HCID 90047746HCID 90047746, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-(6-phenylbenzo[d]thiazol-2-yl)acetohydrazide (105 mg, 0.33 mmol) (described in WO 2011/074560) in MeOH (4 mL) was added potassium bicarbonate (42 mg, 0.42 mmol) followed by cyanogen bromide (0.036 mL, 0.37 mmol) and the reaction mixture stirred for 3 h. The solvent was removed under reduced pressure and the residue purified on silica gel chromatography eluting with 0.5 to 8.5% MeOH/DCM to give Compound 89a (40 mg, 37% yield) as an orange solid. LCMS=1.75 min using analytical method (M), 309.0 (M+H). 1H NMR (400 MHz, CDCl3 containing CD3OD) δ 8.09 (d, J=1.5 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.74 (dd, J=8.5, 1.8 Hz, 1H), 7.68-7.61 (m, 2H), 7.50-7.44 (m, 2H), 7.41-7.36 (m, 1H), 4.59 (s, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified on silica gel chromatography
  3. washeluting with 0.5 to 8.5% MeOH/DCM

Sources & evidence

ORD record
ord-6b3cf456497a4b1e86da266d317a38c5
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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