Hydrochloric Acid → HCID 86695522, compound

HRID 525627Notes

Reaction equation

HRID 525627 reaction equation
[C:1]([CH2:3][CH:4]([NH:31]S(C(C)(C)C)=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C@H:17]3[O:21]C(C)(C)[N:19]([C:24](=[O:28])[CH:25]([F:27])[F:26])[C@@H:18]3[CH2:29][F:30])=[CH:13][CH:12]=2)=[CH:7][N:6]=1)#[N:2].Cl>C(OCC)(=O)C.O1CCOCC1.N>[NH2:31][CH:4]([C:5]1[N:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C@@H:17]([OH:21])[C@H:18]([NH:19][C:24](=[O:28])[CH:25]([F:26])[F:27])[CH2:29][F:30])=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)[CH2:3][C:1]#[N:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86695521HCID 86695521, compound

Product 1

HCID 86695522HCID 86695522, compoundYield 20.8%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid [2-cyano-1-(5-{4-[(4S,5R)-3-(2,2-difluoro-acetyl)-4-fluoromethyl-2,2-dimethyl-oxazolidin-5-yl]-phenyl}-pyridin-2-yl)-ethyl]-amide (0.21 g, 0.392 mmol) in Ethyl acetate (2 mL) is added HCl in dioxane (2.0 mL) at 0° C. The resulting reaction mixture is stirred at room temperature for 3 hours. Solvent is evaporated in vacuo to get the crude residue and diluted with aqueous ammonia solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, concentrated and purified by combi-flash chromatography using 7-8% methanol in CH2Cl2 to afford the title compound (0.032 g): 1HNMR (400 MHz, DMSO-d6) δ: 2.85-2.99 (m, 2H), 4.24-4.35 (m, 2.5H), 4.40-4.44 (m, 0.5H), 4.54-4.55 (m, 0.5H), 4.64-4.67 (m, 0.5H), 4.87-4.88 (m, 2H), 5.92 (d, J=4.44 Hz, 1H), 6.20 (t, J=53.8 Hz, 1H), 7.46 (d, J=8.16 Hz, 2H), 7.62 (d, J=8.16 Hz, 1H), 7.71 (d, J=8.22 Hz, 2H), 8.09-8.12 (dd, J1=2.32 Hz, J2=8.2 Hz, 1H), 8.84-8.87 (m, 2H). LC-MS (m/z): [M+H]=393.0.

Workup

  1. customThe resulting reaction mixture
  2. customSolvent is evaporated in vacuo
  3. customto get the crude residue
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer is dried over sodium sulphate
  6. concentrationconcentrated
  7. custompurified by combi-flash chromatography

Sources & evidence

ORD record
ord-fa387bf2814446ed889f4cad6c04a833
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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