HCID 68182594, compound → HCID 68182549, compound

HRID 1623944Notes

Reaction equation

HRID 1623944 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]3[CH2:19][C@H:20]4[CH2:33][C@H:21]4[C:22]=3[N:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[N:24]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:18]3[CH2:19][C@H:20]4[CH2:33][C@H:21]4[C:22]=3[N:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[N:24]=2)=[O:16])[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 68182594HCID 68182594, compound

Product 1

HCID 68182549HCID 68182549, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-{[(1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.218 mmol) was dissolved in 20% TFA/DCM (3 mL). The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated, and the residue was purified by cation exchange resin to give the title compound (66 mg). LCMS m/z=359.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.48 (td, J=4.2 and 3.6 Hz, 1H), 1.10-1.17 (m, 1H), 1.49-1.55 (m, 2H), 1.97-2.05 (m, 2H), 2.06-2.12 (m, 1H), 2.22-2.29 (m, 1H), 2.78 (t, J=11.1 Hz, 2H), 2.95 (d, J=16.5 Hz, 1H), 3.03 (dd, J=16.4 and 6.2 Hz, 1H), 3.11-3.19 (d, J=11.9 Hz, 2H), 3.97-4.05 (m, 1H), 6.85 (d, J=8.1 Hz, 1H), 6.98-6.74 (m, 2H), 7.61-7.67 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by cation exchange resin

Sources & evidence

ORD record
ord-bc7ece6f44b8416f93527668071fce07
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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