Carbon Tetrachloride → HCID 178433939, compound

HRID 539077Notes

Reaction equation

HRID 539077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]([NH:29][NH:30][C:31](=[NH:33])[CH3:32])=O)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O.C(Cl)Cl.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]5[NH:33][C:31]([CH3:32])=[N:30][N:29]=5)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178465658HCID 178465658, compound

Product 1

HCID 178433939HCID 178433939, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N′-(1-iminoethyl)benzohydrazide (0.049 g, 0.104 mmol) in 1:1 DCM-acetonitrile (10 mL) was treated with carbon tetrachloride (0.040 mL, 0.414 mmol), triethylamine (0.1442 mL, 1.035 mmol) and triphenylphosphine (0.1086 g, 0.414 mmol) at ambient temperature. The mixture was heated at 50° C. for 2 hours. After cooing to ambient temperature, the mixture was treated with EtOAc, washed with water, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-5% MeOH in DCM) to provide (S)-4-(4-fluorophenyl)-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.003 g, 6% yield) as a yellow oil. LCMS (APCI+) m/z 456 [M+H]+.

Workup

  1. customAfter cooing to ambient temperature
  2. washwashed with water
  3. customdried
  4. addition(phase separator silicone treated filter paper)
  5. concentrationconcentrated
  6. custompurified on silica gel (2-5% MeOH in DCM)

Sources & evidence

ORD record
ord-216ee27aa9d741b689b0a5cdbb59023e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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