Triethylamine → HCID 86638553, compound

HRID 1807733Notes

Reaction equation

HRID 1807733 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[Cl:40].[C:41](Cl)(=O)[O:42]C1C=CC([N+]([O-])=O)=CC=1.[NH2:54][CH2:55][C:56]([CH3:59])([OH:58])[CH3:57].C(N(CC)CC)C>ClCCl>[Si:33]([O:32][C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:41]([NH:54][CH2:55][C:56]([OH:58])([CH3:59])[CH3:57])=[O:42])=[C:3]([Cl:40])[CH:4]=3)=[O:9])[CH2:11][CH2:12]2)=[CH:22][CH:21]=1)([C:24]([F:25])([F:26])[F:27])[C:28]([F:31])([F:29])[F:30])([C:36]([CH3:37])([CH3:39])[CH3:38])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86638552(4-Amino-3-chlorophenyl)(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 86638553HCID 86638553, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Amino-3-chlorophenyl)(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)piperazin-1-yl)methanone (0.410 mmol, 250 mg) and 4-nitrophenyl carbonochloridate (0.410 mmol, 83 mg) in dichloromethane (1 ml) were combined and heated at reflux for 1 hour. The reaction was allowed to cool to room temperature before the addition of 1-amino-2-methylpropan-2-ol (0.820 mmol, 73.1 mg) and triethylamine (0.410 mmol, 0.057 mL, 41.5 mg). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the resulting residue was purified by column chromatography (2-5% methanol in dichloromethane) to afford the title compound (190 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customthe resulting residue was purified by column chromatography (2-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3dff86460f2e455f898e6a8aa08630cf
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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