Benzoyl chloride, 3,4,5-trimethoxy- → HCID 16117587, compound

HRID 416597Notes

Reaction equation

HRID 416597 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[S:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[N:20]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:26](Cl)=[O:27]>N1C=CC=CC=1>[N:20]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[S:13][C:12]=1[C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:24]=[C:23]([O:22][CH3:21])[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 59679916HCID 59679916, compound

Product 1

HCID 16117587HCID 16117587, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-amino-5-(thiazolo[5,4-c]pyridin-2-yl)benzoate (150 mg, 0.526 mmol) was mixed together with 3,4,5-trimethoxybenzoyl chloride (121 mg, 0.526 mmol) in 1 mL of pyridine. The reaction mixture was reacted in a Biotage microwave reactor at 160 degrees for 10 min. It was then cooled to room temperature and concentrated. The resulting residue was purified by chromatography using a 9:1 mixture of CH2Cl2 to MeOH to afford 90 mg of methyl 3-(thiazolo[5,4-c]pyridin-2-yl)-5-(3,4,5-trimethoxybenzamido)benzoate (36% yield) (MS, M++H=480).

Workup

  1. customThe reaction mixture was reacted in a Biotage microwave reactor at 160 degrees for 10 min
  2. concentrationconcentrated
  3. customThe resulting residue was purified by chromatography
  4. additiona 9:1 mixture of CH2Cl2 to MeOH

Sources & evidence

ORD record
ord-17365d7c57114d52bfb97bd0089f7973
Source dataset
uspto-grants-2012_01
Patent number
US08088928B2

Reaction notes

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