Trifluoroacetic acid → HCID 67273841, compound

HRID 2264712Notes

Reaction equation

HRID 2264712 reaction equation
C(OC([NH:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:26]2[CH:27]=[CH:28][C:29]([O:40]S(C(F)(F)F)(=O)=O)=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[CH:31]=2)([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[N:10]=1)=O)(C)(C)C.[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>ClCCl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[NH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:26]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[C:29]([OH:40])=[CH:28][CH:27]=2)([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[N:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59596278HCID 59596278, compound

Product 1

HCID 67273841HCID 67273841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [3-(6-hydroxy-3′-methoxy-biphenyl-3-yl)-3-(4-methoxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, F) (10.0 mg, 18.6 umol) was added trifluoroacetic acid in dichloromethane (10%, 1-2 mL) and reaction stirred 60 minutes. The solvents were removed under reduced pressure and the resulting gum put under high vacuum at 50° C. over night to give the title compound as a waxy solid (10.4 mg). 1H NMR (300 MHz, DMSO-d6) δ 8.26 (d, J=7.8 Hz, 1 H), 7.85-7.67 (m, 3 H), 7.32-7.18 (m, 4 H), 7.03-6.85 (m, 8 H), 3.74 (d, J=2.7 Hz, 6 H); MS (APCI+) m/z 437 [M+1]+; tR=2.14 min.

Workup

  1. customThe solvents were removed under reduced pressure
  2. waitthe resulting gum put under high vacuum at 50° C. over night

Sources & evidence

ORD record
ord-75d442f35a404571a0692b463d80ad20
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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