Trifluoroacetic acid → HCID 86695525, compound

HRID 525629Notes

Reaction equation

HRID 525629 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C@H:21]3[O:25]C(C)(C)[N:23]([C:28](=[O:32])[CH:29]([F:31])[F:30])[C@@H:22]3[CH2:33][F:34])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>C(Cl)Cl>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[NH2:7][CH2:8][C:9]1[N:10]=[N:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C@@H:21]([OH:25])[C@H:22]([NH:23][C:28](=[O:32])[CH:29]([F:30])[F:31])[CH2:33][F:34])=[CH:19][CH:20]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695524HCID 86695524, compound

Product 1

HCID 86695525HCID 86695525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (6-{4-[(4S,5R)-3-(2,2-Difluoro-acetyl)-4-fluoromethyl-2,2-dimethyl-oxazolidin-5-yl]-phenyl}-pyridazin-3-ylmethyl)-carbamic acid tert-butyl ester (0.25 g, 0.506 mmol) in CH2Cl2 (10 mL) is added trifluoroacetic acid (1.5 mL) at room temperature. Resulting reaction mixture is allowed to stir at room temperature for 5 h. The solvent evaporated in vacuo and the crude material is striped out with CH2Cl2 followed by washing with n-pentane and diethyl ether and dried to afford title compound (0.181 g): 1H NMR (400 MHz, DMSO-d6) 4.32-4.39 (m, 1.5H), 4.46 (m, 2.5H), 4.55-4.58 (m, 0.5H), 4.68-4.71 (m, 0.5H), 4.94 (bs, 1H), 5.99 (bs, 1H), 6.19 (t, J=53.76 Hz, 1H), 7.54 (d, J=8.28 Hz, 2H), 7.85 (d, J=8.92 Hz, 1H), 8.13 (d, J=8.32 Hz, 2H), 8.36 (d, J=10 HZ, 1H), 8.51 (bs, 2H), 8.87 (d, J=8.72 Hz, 1H). LC-MS (m/z): [M+H]=355.

Workup

  1. customResulting
  2. customreaction mixture
  3. customThe solvent evaporated in vacuo
  4. washby washing with n-pentane and diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-5700e054a3234e34b9143bc9a7543f65
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

Loading…