Trifluoroacetic acid → HCID 178507116, compound

HRID 1037265Notes

Reaction equation

HRID 1037265 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][C:27]5[N:28]=[CH:29][N:30](COCC[Si](C)(C)C)[C:31]=5[C:21]=4[O:20][C:19]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(OC(=O)NC1(C2C=CC(C3C(=O)C4C=CC5N(COCC[Si](C)(C)C)C=NC=5C=4OC=3C3C=CC=CC=3)=CC=2)CCC1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][C:27]5[N:28]=[CH:29][NH:30][C:31]=5[C:21]=4[O:20][C:19]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67067791HCID 67067791, compoundHCID 68227556HCID 68227556, compound

Product 1

HCID 178507116HCID 178507116, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution, containing a mixture of (1-{-4-[6-oxo-8-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester and (1-{4-[6-oxo-8-phenyl-3-(2-trimethylsilanyl-ethoxymethyl)-3,6-dihydro-chromeno[7,8-d]imidazol-7-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (11 mg, 0.017 mmol), in DCM (1.0 mL) was added TFA (0.25 mL). The reaction mixture was stirred at RT for 18 h. After this time the reaction mixture was concentrated in vacuo. The resultant residue was triturated with DCM (×2) and dried in vacuo to furnish the title compound (7.4 mg, 84%). LCMS (Method E): RT=2.76 min, [M+]+=408. 1H NMR (400 MHz, DMSO-d6): 8.69 (s, 1H), 8.67 (br s, 1H), 8.12 (d, J=8.6 Hz, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.71-7.61 (m, 5H), 7.59-7.51 (m, 4H), 2.84-2.75 (m, 2H), 2.74-2.64 (m, 2H), 2.40-2.28 (m, 1H), 2.07-1.95 (m, 1H).

Workup

  1. additionTo a solution, containing
  2. concentrationAfter this time the reaction mixture was concentrated in vacuo
  3. customThe resultant residue was triturated with DCM (×2)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-29468c5e90854b36a472217772ee7842
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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