Carbon Tetrachloride → HCID 178433940, compound

HRID 539004Notes

Reaction equation

HRID 539004 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl.[NH:32]=[C:33]([NH:35][NH:36][C:37](=O)[C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:45]=[N:46][N:47]3[CH:52]=[CH:51][C:50]([N:53]4[C@@H:57]([CH:58]([CH3:60])[CH3:59])[CH2:56][O:55][C:54]4=[O:61])=[N:49][C:48]=23)=[CH:40][CH:39]=1)[CH3:34]>ClCCl.CC#N.CCOC(C)=O>[CH:58]([C@H:57]1[CH2:56][O:55][C:54](=[O:61])[N:53]1[C:50]1[CH:51]=[CH:52][N:47]2[N:46]=[CH:45][C:44]([C:41]3[CH:40]=[CH:39][C:38]([C:37]4[NH:32][C:33]([CH3:34])=[N:35][N:36]=4)=[CH:43][CH:42]=3)=[C:48]2[N:49]=1)([CH3:59])[CH3:60]

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178465659HCID 178465659, compound

Product 1

HCID 178433940HCID 178433940, compoundYield 18.3%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

PS-Triphenylphosphine resin (Biotage, catalog No. 800380, 2.28 mmol/g, 0.167 g, 0.38 mmol)triethylamine (0.132 mL, 0.95 mmol), and CCl4 (40 μL, 0.38 mmol) were added to a suspension of (S)—N′-(1-iminoethyl)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (40 mg, 0.095 mmol) in dichloromethane (3 mL) and MeCN (3 mL), and the reaction mixture was heated to 50° C. for 2 hours. After cooling to ambient temperature, the mixture was treated with EtOAc, washed with water, dried over MgSO4, concentrated under reduced pressure. The crude was purified by silica gel flash column chromatography (4% MeOH in dichloromethane) to afford 7 mg (18%) of (S)-4-isopropyl-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one. 1H NMR (400 MHz, CD3OD/CDCl3) δ 8.70 (d, 1H), 8.48 (s, 1H), 8.13 (m, 2H), 8.05 (m, 3H), 5.05 (m, 1H), 4.50 (m, 2H), 2.92 (m, 1H), 2.52 (s, 3H), 1.12 (d, 3H), 0.96 (d, 3H); LCMS (APCI+) m/z 404.3 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by silica gel flash column chromatography (4% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-32f239b3c954405b9b4d70e9fef1e34d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…