3-Aminophenyl dimethylcarbamate → HCID 67036855, compound

HRID 216074Notes

Reaction equation

HRID 216074 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:55][N:56]([CH3:67])[C:57](=[O:66])[O:58][C:59]1[CH:64]=[CH:63][CH:62]=[C:61]([NH2:65])[CH:60]=1>C(OC(C)C)(=O)C.CCOC(C)=O>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][C:11]1([C:14](=[O:15])[NH:65][C:61]2[CH:62]=[CH:63][CH:64]=[C:59]([O:58][C:57](=[O:66])[N:56]([CH3:55])[CH3:67])[CH:60]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 298773-Aminophenyl dimethylcarbamateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670368571-(Tert-butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acid

Product 1

HCID 67036855HCID 67036855, compound

Reagents, catalysts & solvents 2

HCID 7915Isopropyl AcetateSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

1-(tert-Butoxycarbonyl)-4-(2-(dimethylamino)ethyl)piperidine-4-carboxylic acid from step B (100 mg, 0.33 mmol), HATU (175 mg, 0.46 mmol), and N,N-diisopropylethylamine (0.116 mL, 0.67 mmol) were stirred in isopropyl acetate for 10 minutes. 3-aminophenyl dimethylcarbamate (90 mg, 0.5 mmol) was added, and the reaction was stirred at 85° C. for 2 hours, cooled to room temperature, stirred overnight, and then diluted with EtOAc, washed with sat. aq. Na2CO3 and brine (with back extraction), dried over MgSO4, filtered, and concentrated under vacuum, to give the title compound as a viscous oil. MS (ES+) [M+H]+=463.

Workup

  1. temperaturecooled to room temperature
  2. stirringstirred overnight
  3. washwashed with sat. aq. Na2CO3 and brine (with back extraction)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-be9ba0704e534dcb843e516760891a53
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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