Trifluoroacetic acid → HCID 59472315, compound

HRID 78675Notes

Reaction equation

HRID 78675 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15](C(OC(C)(C)C)=O)[C:16]1[C:17]([C:36]2[O:40][N:39]=[C:38]([C:41]3[CH:46]=[CH:45][C:44]([CH2:47][N:48](C)[C:49](=O)OC(C)(C)C)=[CH:43][C:42]=3[F:57])[CH:37]=2)=[N:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH:31]3[CH2:35][CH2:34][O:33][CH2:32]3)(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[CH:20][N:21]=1)=O)(C)(C)C>ClCCl>[F:57][C:42]1[CH:43]=[C:44]([CH2:47][NH:48][CH3:49])[CH:45]=[CH:46][C:41]=1[C:38]1[CH:37]=[C:36]([C:17]2[C:16]([NH2:15])=[N:21][CH:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH:31]4[CH2:35][CH2:34][O:33][CH2:32]4)(=[O:29])=[O:30])=[CH:24][CH:23]=3)[N:18]=2)[O:40][N:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59472412HCID 59472412, compound

Product 1

HCID 59472315HCID 59472315, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (281.6 mg, 190.3 μL, 2.470 mmol) was added to a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-tetrahydrofuran-3-ylsulfonylphenyl)pyrazin-2-yl]isoxazol-3-yl]-3-fluoro-phenyl]methyl]-N-methyl-carbamate (100 mg, 0.1235 mmol) in dichloromethane (2.069 mL) at room temperature and the resulting solution stirred for 2 h. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]. The product fractions were collected and lypholised to give the product as a yellow solid (34.0 mg, 44% yield); 1H NMR (400.0 MHz, DMSO) d 2.13-2.19 (m, 2H), 2.63 (m, 3H), 3.66 (m, 1H), 3.76 (m, 1H), 3.85 (m, 1H), 4.04 (m, 1H), 4.21-4.28 (m, 3H), 7.27 (m, 2H), 7.52 (m, 1H), 7.60-7.65 (m, 2H), 8.00 (m, 2H), 8.12 (t, 1H), 8.36 (m, 2H) and 8.94 (m, 3H) ppm; MS (ES+) 510.2

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3 CN) over 16 minutes at 25 mL/min]
  3. customThe product fractions were collected

Sources & evidence

ORD record
ord-e3513916a26c40ecbcf44d6feb0f737c
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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