2-Amino-4-methylthiazole → HCID 86607491, compound

HRID 550584Notes

Reaction equation

HRID 550584 reaction equation
[C:1]([O:5][C:6]([N:8]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:9]1[C:10]([C:15]([OH:17])=O)=[N:11][CH:12]=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[S:26][CH:27]=[C:28]([CH3:30])[N:29]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[C:10]([C:15](=[O:17])[NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[N:11][CH:12]=[CH:13][N:14]=1)[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 741432-Amino-4-methylthiazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67151993HCID 67151993, compound

Product 1

HCID 86607491HCID 86607491, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(tert-Butoxycarbonyl-pyridin-3-yl-amino)-pyrazine-2-carboxylic acid (405 mg, 80%, 1.02 mmol), 2-amino-4-methylthiazole (129 mg, 1.12 mmol), N,N-diisopropylethylamine (0.23 ml, 1.33 mmol) and TBTU (430 mg, 1.33 mmol) were dissolved in 1 ml DMF and stirred over night at room temperature. The reaction mixture was quenched with water and extracted two times with ethyl acetate. The organic extracts were washed with 2N NaOH-solution, water and brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->40:60 gradient). The desired compound was obtained as a yellow foam (195 mg, 46%), MS: m/e=413.3 (M+H+).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted two times with ethyl acetate
  3. washThe organic extracts were washed with 2N NaOH-solution, water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->40:60 gradient)

Sources & evidence

ORD record
ord-3cff1ee2d94f410d97b6aef892cdd70e
Source dataset
uspto-grants-2011_05
Patent number
US07947685B2

Reaction notes

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