Acetyl chloride → Trifluoroacetic acid

HRID 707130Notes

Reaction equation

HRID 707130 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.[OH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[O:10].[CH:15]12[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][N:17]([C:23]1[N:28]=[C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:26]=[C:25]([C:35]3[CH:40]=[CH:39][C:38]([NH:41][C:42]([NH:44][C:45]4[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=4)=[O:43])=[CH:37][CH:36]=3)[N:24]=1)[CH2:16]2.C(Cl)(=O)C>ClCCl.C(N(CC)CC)C>[C:2]([N:32]1[CH2:33][CH2:34][N:29]([C:27]2[N:28]=[C:23]([N:17]3[CH2:16][CH:15]4[O:22][CH:19]([CH2:20][CH2:21]4)[CH2:18]3)[N:24]=[C:25]([C:35]3[CH:36]=[CH:37][C:38]([NH:41][C:42]([NH:44][C:45]4[CH:46]=[CH:47][N:48]=[CH:49][CH:50]=4)=[O:43])=[CH:39][CH:40]=3)[N:26]=2)[CH2:30][CH2:31]1)(=[O:1])[CH3:4].[C:9]([OH:10])([C:11]([F:14])([F:13])[F:12])=[O:8]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 130403997HCID 130403997, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44548794HCID 44548794, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(piperazin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea-2TFA (230 mg) in dichloromethane (4 mL) and triethylamine (1 mL) was treated with acetyl chloride. The mixture was concentrated to dryness and purified on HPLC to give the title compound as its TFA salt; MS (ES+) 530.3 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompurified on HPLC

Sources & evidence

ORD record
ord-e254ab06a3a44c00959dd607db0636dc
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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