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Methyl chloroformate → Trifluoroacetic acid

HRID 707133
Notes
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Reaction equation

HRID 707133 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].OC(C(F)(F)F)=O.[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(N(CC)CC)C.Cl[C:59]([O:61][CH3:62])=[O:60]>ClCCl.O1CCCC1>[CH:19]12[O:22][CH:15]([CH2:21][CH2:20]1)[CH2:16][N:17]([C:23]1[N:24]=[C:25]([C:35]3[CH:36]=[CH:37][C:38]([NH:41][C:42](=[O:43])[NH:44][C:45]4[CH:46]=[CH:47][N:48]=[CH:49][CH:50]=4)=[CH:39][CH:40]=3)[N:26]=[C:27]([N:29]3[CH2:34][CH2:33][N:32]([C:59]([O:61][CH3:62])=[O:60])[CH2:31][CH2:30]3)[N:28]=1)[CH2:18]2.[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 130403997HCID 130403997, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44548797HCID 44548797, compound

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent

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 (75 mg) in dichloromethane (2 mL), tetrahydrofuran (2 mL), and triethylamine (1 mL) was treated with methyl chloroformate (0.10 mL). The mixture was concentrated to dryness and purified on RP-HPLC to give the title compound as its TFA salt. MS (ES+) 546.3 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-9c09c91bad8d4550b67588e15c8be073
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174963B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes