Sodium Bicarbonate → tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamate

HRID 1727370Notes

Reaction equation

HRID 1727370 reaction equation
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)=O.C1([CH2:33][CH2:34][C:35]([NH2:37])=[S:36])C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:12][C:8]1[CH:7]=[C:6]([C:4]2[N:37]=[C:35]([CH2:34][CH3:33])[S:36][C:3]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:14]=2)[CH:11]=[CH:10][CH:9]=1.[NH2:19][C:15]1[CH:14]=[C:13]([C:3]2[S:36][C:35]([CH2:34][CH3:33])=[N:37][C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=2)[CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 51507353-PhenylpropanethioamideHCID 229326522-Bromo-1-(3-bromophenyl)-2-[2-(boc-amino)-4-pyridyl]ethanone hydrocbromide

Product 2

HCID 229326504-[4-(3-Bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-amineYield 8%HCID 22932827tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamateYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-1-(3-bromophenyl)-2-[2-(tert-butoxycarbonylamino)-4-pyridyl]ethanone hydrobromide (22 g, 51 mmol) in N,N,-dimethylformamide (100 mL) was added thiopropionamide (4.3 g, 49 mmol), and the mixture was stirred for 2 hours at room temperature. Into the reaction mixture was poured an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1), then, recrystallized from hexane-ethyl acetate to obtain 4-(3-bromophenyl)-5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-1,3-thiazole (6.0 g, yield 27%) and 5-(2-amino-4-pyridyl)-4-(3-bromophenyl)-2-ethyl-1,3-thiazole (1.4 g, yield 8%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)
  6. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-df244dbe4b4645d3b895abdf2477d0b3
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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