Trifluoroacetic acid → HCID 53476392, compound

HRID 1253576Notes

Reaction equation

HRID 1253576 reaction equation
[CH:1]1([NH:4][C:5](=[O:45])[NH:6][C:7]2[CH:43]=[CH:42][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:26]=[CH:25][C:24]([CH2:27][N:28]([CH2:36][CH2:37][S:38]([CH3:41])(=[O:40])=[O:39])C(=O)OC(C)(C)C)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:44])[CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:43]=[CH:42][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH:22]=[CH:23][C:24]([CH2:27][NH:28][CH2:36][CH2:37][S:38]([CH3:41])(=[O:39])=[O:40])=[CH:25][N:26]=5)[S:20][C:13]=34)=[C:9]([F:44])[CH:8]=2)=[O:45])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67442547HCID 67442547, compound

Product 1

HCID 53476392HCID 53476392, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 99 (120 mg, 0.18 mmol) in DCM (20 mL) was added TFA (5.6 mL). The reaction mixture was stirred at RT overnight, concentrated, diluted with ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV), to afford the title compound 100 (90 mg, 0.13 mmol, 72% yield, TFA salt) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) δ 8.74 (s, 1H), 8.60 (s, 1H), 8.52 (d, J=5.2 Hz, 1H), 8.34 (s, 1H), 8.26 (d, J=8.4 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=8.8 Hz, 1H), 7.20 (d, J=10.0 Hz, 1H), 6.64 (d, J=5.2 Hz, 1H), 6.61 (s, 1H), 3.84 (s, 2H), 3.35-3.25 (m, 2H), 3.05 (s, 3H), 3.02-2.90 (m, 2H), 2.59-2.50 (m, 1H), 0.69-0.62 (m, 2H), 0.46-0.40 (m, 2H). MS (m/z): 556.5 (M+H).

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV)

Sources & evidence

ORD record
ord-4580c0651b52409689ce8fa455ba80d8
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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