Methyl chloroacetate → HCID 67520661, compound

HRID 1926372Notes

Reaction equation

HRID 1926372 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:30][O:31][C:32](=[O:35])[CH2:33]Cl.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][CH2:33][C:32]([O:31][CH3:30])=[O:35])=[CH:4][C:3]=1[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1

Participants

6

Reactant 4

HCID 7295Methyl chloroacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 675207593-[6-Amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenol

Product 1

HCID 67520661HCID 67520661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[6-amino-5-(1,3-benzothiazol-2-yl)pyridin-3-yl]phenol (80 mg, 0.20 mmol), potassium carbonate (100 mg, 0.700 mmol) and chloroacetic acid methyl ester (33 mg, 0.30 mmol) in DMF was left to stir at rt overnight. To the mixture was added EtOAc (10 mL), which was left to stir at rt for 10 min. Then, the mixture was washed with NaHCO3 aq. soln. (2×). The combined organic extracts were treated with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification via silica gel chromatography (5% MeOH in DCM) afforded the title compound as a yellow solid. MS (ES+): m/z=392.02 (100) [MH+]. HPLC: tR=3.63 min (ZQ3, polar—5 min).

Workup

  1. waitwas left
  2. stirringto stir at rt for 10 min
  3. washThen, the mixture was washed with NaHCO3 aq. soln
  4. additionThe combined organic extracts were treated with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-49045580cc154653a5059044358d3d40
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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