Hydrogen Bromide → HCID 11201703, compound

HRID 2222211Notes

Reaction equation

HRID 2222211 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[S:9][CH:10]=1)=[O:5])[CH3:2].Br.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]([C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[Cl:23])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 75176664HCID 75176664, compound

Product 1

HCID 11201703HCID 11201703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.18 g (7.1 mmol) 2-(3,4-Dimethoxy-phenylamino)-thiazole-4-carboxylic acid ethyl ester; hydrobromide, 1.87 g (10.7 mmol) 2-Chlorobenzoyl chloride and 2.96 ml (21.4 mmol) NEt3 in 30 ml DCM was stirred at room temperature for 24 h. After evaporation of the volatiles the residue was taken up in MeOH and purified with flash column chromatography on silica eluting with a gradient of heptane/ethyl acetate to yield after evaporation of the product fractions 1.58 g (50%) of the title compound. MS (m/e): 446.9 (MH+, 100%)

Workup

  1. customAfter evaporation of the volatiles the residue
  2. custompurified with flash column chromatography on silica eluting with a gradient of heptane/ethyl acetate
  3. customto yield
  4. customafter evaporation of the product fractions 1.58 g (50%) of the title compound

Sources & evidence

ORD record
ord-ab50a7855c6b41beb1923f5ea10a8b69
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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