Trifluoroacetic acid → Trifluoroacetic acid

HRID 588473Notes

Reaction equation

HRID 588473 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C(OC([N:15]1[CH2:20][CH2:19][C@H:18]([N:21]2[C:33]3[C:32]4[CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][C:37]([O:40][C:41]6[N:46]=[CH:45][CH:44]=[CH:43][N:42]=6)=[CH:36][C:35]=5[Cl:47])[C:29]([F:48])=[CH:28][C:27]=4[N:26]=[CH:25][C:24]=3[N:23]=[C:22]2[CH3:49])[C@@H:17]([F:50])[CH2:16]1)=O)(C)(C)C.CO.C(Cl)Cl>C(Cl)Cl>[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[Cl:47][C:35]1[CH:36]=[C:37]([O:40][C:41]2[N:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:38]=[CH:39][C:34]=1[C:30]1[C:29]([F:48])=[CH:28][C:27]2[N:26]=[CH:25][C:24]3[N:23]=[C:22]([CH3:49])[N:21]([C@H:18]4[CH2:19][CH2:20][NH:15][CH2:16][C@@H:17]4[F:50])[C:33]=3[C:32]=2[CH:31]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 117876256HCID 117876256, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 117876816HCID 117876816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (20 ml) was added drop wise to a solution of (3S,4S)-tert-butyl-4-(8-(2-chloro-4-(pyrimidin-2-yloxy)phenyl)-7-fluoro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-3-fluoropiperidine-1-carboxylate (10 g, 0.0164 mol) in dry DCM (150 mL) at 0° C. under N2 atmosphere. After addition completed, the reaction mixture allowed to RT and stirred for 3 h. The reaction was monitored by TLC (5% MeOH/DCM), after completion of reaction by TLC, the volatiles were concentrated under vacuum. The obtained residue was triturated with diethyl ether. The solid was filtered and dried under vacuum to afford TFA salt of 8-(2-chloro-4-(pyrimidin-2-yloxy)phenyl)-7-fluoro-1-((3S,4S)-3-fluoropiperidin-4-yl)-2-methyl-1H-imidazo[4,5-c]quinoline (11 g, quantitative). LCMS: 99.41%, m/z=507.1 (M+1) (Free base); HPLC: 96.43%, 6.002 min.

Workup

  1. additionAfter addition
  2. customallowed to RT
  3. customafter completion of reaction by TLC
  4. concentrationthe volatiles were concentrated under vacuum
  5. customThe obtained residue was triturated with diethyl ether
  6. filtrationThe solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-26e854886f404b22b701010d506b8218
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

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