Diisopropylethylamine → HCID 67438282, compound

HRID 1185332Notes

Reaction equation

HRID 1185332 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:20])[C:6]=1[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:63]([O:67][C:68]([NH:70][C:71]1[S:75][C:74]([C:76]2[C:81]([F:82])=[CH:80][CH:79]=[CH:78][C:77]=2[F:83])=[N:73][C:72]=1[C:84](O)=[O:85])=[O:69])([CH3:66])([CH3:65])[CH3:64]>C(Cl)Cl>[F:83][C:77]1[CH:78]=[CH:79][CH:80]=[C:81]([F:82])[C:76]=1[C:74]1[S:75][C:71]([NH:70][C:68](=[O:69])[O:67][C:63]([CH3:65])([CH3:64])[CH3:66])=[C:72]([C:84](=[O:85])[NH:1][C:2]2[CH:3]=[N:4][N:5]([CH3:20])[C:6]=2[C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:9][CH:8]=2)[N:73]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58464827HCID 58464827, compoundHCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 67438282HCID 67438282, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (85 mg, 0.31 mmol) in DCM (20 mL) was added DIPEA (0.5 mL, 2.87 mmol), PyBOP (0.238 g, 0.46 mmol) and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (0.114 g, 0.32 mmol) and the mixture was stirred at room temperature for 18 hr. The mixture was diluted with DCM and washed with water. The organic layer was separated, dried over MgSO4 and the solvent removed under reduced pressure. Purification via silica gel column chromatography (0-75% EtOAc/isohexane) gave tert-butyl 2-(2,6-difluorophenyl)-4-(1-methyl-5-(tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate as a white solid (54 mg, 29%).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customthe solvent removed under reduced pressure
  5. customPurification via silica gel column chromatography (0-75% EtOAc/isohexane)

Sources & evidence

ORD record
ord-0f3b9e21af404bf6b98a3f81d9ebd7b9
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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