Trifluoroacetic acid → HCID 66673149, compound

HRID 423559Notes

Reaction equation

HRID 423559 reaction equation
CC([N:5]([CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]3[CH2:34][CH2:33][N:32]([C:35]4[O:39][N:38]=[C:37]([CH:40]([CH3:42])[CH3:41])[N:36]=4)[CH2:31][CH2:30]3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])C(=O)[O-])(C)C.[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44]>C(Cl)Cl>[C:43]([OH:49])([C:45]([F:48])([F:47])[F:46])=[O:44].[F:46][C:45]([F:48])([F:47])[C:43]([OH:49])=[O:44].[NH2:5][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH:29]3[CH2:30][CH2:31][N:32]([C:35]4[O:39][N:38]=[C:37]([CH:40]([CH3:42])[CH3:41])[N:36]=4)[CH2:33][CH2:34]3)=[CH:25][CH:26]=2)=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86638740HCID 86638740, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.05%HCID 66673149HCID 66673149, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl{2-[({4′-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]-4-biphenylyl}sulfonyl)amino]ethyl}carbamate (Example 108, 160 mg, 0.27 mmol) and TFA (0.3 mL) in CH2Cl2 (3 mL) was stirred at ambient temperature for 1 h. The crude product was concentrated and purified by reverse-phase preparative HPLC using a CH3CN:H2O gradient (0.5:99.5 to 90:10) with 0.05% TFA as a modifier to give 123 mg (91%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.09 (bs, 2H), 7.86 (d, 2H, J=8.2 Hz), 7.60 (d, 2H, J=8.2 Hz), 7.46 (d, 2H, J=8.8 Hz), 7.33 (bs, 1H), 6.92 (d, 2H, J=8.8 Hz), 4.24-4.14 (m, 2H), 3.84 (d, 2H, J=6.2 Hz), 3.27 (bs, 4H), 3.14-3.04 (m, 2H), 2.94-2.81 (m, 1H), 2.10-2.00 (m, 1H), 1.98-1.88 (m, 2H), 1.51-1.37 (m, 2H), 1.27 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 500 (M+H).

Workup

  1. concentrationThe crude product was concentrated
  2. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-3822a46327e6483fbc79932474158a34
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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