Trifluoroacetic acid → HCID 68227533, compound

HRID 1037304Notes

Reaction equation

HRID 1037304 reaction equation
[Cl:1][C:2]1[C:11]2[N:12]([CH3:15])[CH:13]=[N:14][C:10]=2[C:9]2[O:8][C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:6]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4([NH:32]C(=O)O)[CH2:31][CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:5](=[O:36])[C:4]=2[CH:3]=1.C(OC(=O)NC1(C2C=CC(C3C(=O)C4C=C(Cl)C5N=CN(C)C=5C=4OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.O.Cl>[ClH:1].[NH2:32][C:28]1([C:25]2[CH:24]=[CH:23][C:22]([C:6]3[C:5](=[O:36])[C:4]4[CH:3]=[C:2]([Cl:1])[C:11]5[N:12]([CH3:15])[CH:13]=[N:14][C:10]=5[C:9]=4[O:8][C:7]=3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:27][CH:26]=2)[CH2:29][CH2:30][CH2:31]1

Participants

8

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67067778HCID 67067778, compoundHCID 86671037HCID 86671037, compound

Product 1

HCID 68227533HCID 68227533, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {1-[4-(4-chloro-3-methyl-6-oxo-8-phenyl-3,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tea-butyl ester and {1-[4-(4-chloro-1-methyl-6-oxo-8-phenyl-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (43 mg, 0.08 mmol) in DCM (1.5 mL) was added TFA (0.5 mL) at RT. After 1 h, the reaction mixture was concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 20% MeOH in DCM) to yield a white solid. This crude residue was dissolved in a mixture of MeOH (0.5 mL), water (1.5 mL) and 1 M HCl (0.1 mL) and chromatographed on a 10 g C18 cartridge {30 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (4.0 mg). LCMS (Method E): RT=3.27 min, [M÷H]+=456/458. 1H NMR (300 MHz, CD3OD): δ 8.40 (s, 1H), 7.99 (s, 1H), 7.60-7.49 (m, 4H), 7.47-7.30 (m, 5H), 4.29 (s, 3H), 2.86-2.58 (m, 4H), 2.36-2.22 (m, 1H), 2.06-1.92 (m, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto yield a white solid
  3. customchromatographed on a 10 g C18 cartridge

Sources & evidence

ORD record
ord-68ed358361934e28803804972754ed77
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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