Carbon Tetrachloride → HCID 70168482, compound

HRID 1426948Notes

Reaction equation

HRID 1426948 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([CH2:27]O)=[C:20]2[N:19]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC(Cl)(Cl)Cl>C(Cl)Cl>[F:12][C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[O:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:27][C:26]1=[C:20]3[N:19]=[C:18]([CH:23]=[CH:22][N:21]3[N:24]=[CH:25]1)[N:14]1[C@@H:13]2[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 67470773HCID 67470773, compound

Product 1

HCID 70168482HCID 70168482, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-(5-(2-(2-(3-aminoprop oxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)methanol (50 mg, 0.130 mmol), PS—PPh3 (0.259 mmol) and perchloromethane (200 mg, 1.30 mmol) in DCM (5 mL) was shaken at ambient temperature overnight. The reaction was filtered, concentrated and purified by reverse-phase column chromatography eluting with 0-60% acetonitrile/H2O to yield the title product (27.4 mg, 57.5% yield). MS (apci) m/z=368.1 (M+H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by reverse-phase column chromatography
  4. washeluting with 0-60% acetonitrile/H2O

Sources & evidence

ORD record
ord-28cba05477af4037a134b22bcebb4f9a
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

Loading…