Cyclopropanemethanol → HCID 59175879, compound

HRID 1807728Notes

Reaction equation

HRID 1807728 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]([OH:32])([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[F:33].[C:34](Cl)(=[O:45])[O:35][C:36]1[CH:41]=[CH:40][C:39]([N+]([O-])=O)=CC=1.C1(CO)CC1>ClCCl>[F:33][C:3]1[CH:4]=[C:5]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:30])([F:31])[F:29])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[O:9])[CH:6]=[CH:7][C:2]=1[NH:1][C:34](=[O:45])[O:35][CH2:36][CH:41]1[CH2:39][CH2:40]1

Participants

5

Reactant 3

HCID 75644CyclopropanemethanolHCID 821294-Nitrophenyl chloroformateHCID 86638550(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 59175879HCID 59175879, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-benzyl)piperazin-1-yl)methanone (0.209 mmol, 0.1 g) and 4-nitrophenyl carbonochloridate (0.209 mmol, 0.042 g) were combined and stirred in dichloromethane (1 mL) at room temperature for 30 minutes. Cyclopropylmethanol (0.417 mmol, 0.030 g) and N,N-dimethylaminopyridine (0.003 g, 0.0209 mmol) were added and the reaction stirred at room temperature for 17 hours. The reaction was concentrated under vacuum and purified by acidic reverse phase HPLC to afford the title compound (22 mg).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. custompurified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-f5e68571f65140a5a96b5738b9110cb4
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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