tert-Butyl carbazate → HCID 57978675, compound

HRID 1866857Notes

Reaction equation

HRID 1866857 reaction equation
CC[N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5].[C:10]1([C:16]2([C:23]3[CH:31]=[C:30]([O:32]CC4C=CC5C(=CC=CC=5)N=4)[CH:29]=[CH:28][C:24]=3[C:25](O)=[O:26])[CH2:21][CH:20]3[CH2:22][CH:17]2[CH2:18][CH2:19]3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:44]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:47])[NH:45][NH2:46].CN(C(ON1N=N[C:63]2[CH:64]=CC=N[C:62]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:77](=O)(O)[O-].[Na+]>CN(C=O)C>[C:49]([O:48][C:44]([NH:45][NH:46][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:30]([O:32][CH2:9][C:7]2[CH:8]=[CH:77][C:5]3[C:4](=[CH:6][CH:62]=[CH:63][CH:64]=3)[N:3]=2)=[CH:31][C:23]=1[C:16]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:21][CH:20]2[CH2:22][CH:17]1[CH2:18][CH2:19]2)=[O:47])([CH3:52])([CH3:51])[CH3:50]

Participants

7

Reactant 5

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44447720HCID 44447720, compound

Product 1

HCID 57978675HCID 57978675, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (1.53 mL, 8.78 mmol.) was added to a stirred solution of 4b (1.76 mmol), t-butyl carbazate (1.16 g, 8.78 mmol) and HATU (1.34 g, 3.52 mmol) in DMF (20 mL) at ambient temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0-35% EtOAc/hexanes as eluent) furnished the title compound 4c, m/z (ES) 564 (MH)+.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0-35% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-6c806e072c0844cf90e242cd681c24df
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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