Trifluoroacetic acid → HCID 25155417, compound

HRID 509294Notes

Reaction equation

HRID 509294 reaction equation
CC([N:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2S[CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]([O:33][CH2:34][C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[O:32])=[CH:25][CH:24]=1)=[O:22])C(=O)[O-])(C)C.[C:41](O)([C:43](F)(F)F)=O>C(Cl)Cl>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([CH2:34][O:33][C:31](=[O:32])[NH:30][CH2:29][C:26]2[CH:27]=[CH:28][C:23]([C:21]([NH:20][C:10]3[CH:11]=[C:12]([C:15]4[CH:43]=[CH:41][CH:17]=[CH:18][CH:19]=4)[CH:13]=[CH:14][C:9]=3[NH2:5])=[O:22])=[CH:24][CH:25]=2)[CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131730272HCID 131730272, compound

Product 1

HCID 25155417HCID 25155417, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl[2-[({4-[({[(pyridin-3-ylmethyl)oxy]carbonyl}amino)methyl]phenyl}carbonyl)amino]-4-(2-thienyl)phenyl]carbamate (10.5 g, 19 mmol) was taken up in DCM (208 mL)/TFA (41.7 mL). After 1 hour, the solvent was removed in vacuo, saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give pyridin-3-ylmethyl[(4-{[(4-aminobiphenyl-3-yl)amino]carbonyl}phenyl)methyl]carbamate as a tan solid. 1H NMR (d6-DMSO, 600 MHz) δ 9.69 (s, 1H), 8.57 (s, 1H), 8.51 (dd, J=4.8 and 1.8 Hz, 1H), 7.94 (m, 3H), 7.77 (d, J=7.8 Hz, 1H), 7.53 (d, J=7.8 Hz, 2H), 7.50 (d, J=1.8 Hz, 1H), 7.37 (m, 5H), 7.31 (dd, J=8.4 and 1.8 Hz, 1H), 7.22 (t, J=7.8 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 5.08 (br s, 4H), 4.26 (d, J=6.0 Hz, 2H). MS: cal'd 453 (MH+), exp 453 (MH+).

Workup

  1. customthe solvent was removed in vacuo, saturated NaHCO3
  2. additionwas added
  3. extractionthe products extracted into EtOAc (×2)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c6bd1a6b8364a8fac5603d8616fbed3
Source dataset
uspto-grants-2015_08
Patent number
US09096559B2

Reaction notes

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