Oxalyl chloride → HCID 67131114, compound

HRID 1678684Notes

Reaction equation

HRID 1678684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18]([OH:20])=[O:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.[C:27](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:27][O:19][C:18](=[O:20])[CH:17]([C:16]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[C:10]2[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 67131112[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 67131114HCID 67131114, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (250 mg, 0.67 mmol; example 5.1) in dry DCM (7 mL) was added oxalyl chloride (0.14 ml, 1.67 mmol) drop wise at 0° C. followed by 1 drop DMF and the reaction mixture was stirred at that temperature for 30 min. Ice-bath was removed and stirring was continued for 3.5 h at room temperature. DCM and excess oxalyl chloride was then removed under reduced pressure and MeOH (2 ml) was then added to it at 0° C. After being stirring the reaction mixture at rt for 1 h, TLC shows formation of a new spot. MeOH was removed under vacuo and crude material was passed through a bed of silica gel (SiO2, 100-200 mesh, EtOAc:hexane 30:70) to give the title compound as colorless liquid (250 mg, 95.5%).

Workup

  1. customIce-bath was removed
  2. stirringstirring
  3. waitwas continued for 3.5 h at room temperature
  4. customDCM and excess oxalyl chloride was then removed under reduced pressure and MeOH (2 ml)
  5. additionwas then added to it at 0° C
  6. stirringAfter being stirring the reaction mixture at rt for 1 h
  7. customMeOH was removed under vacuo and crude material

Sources & evidence

ORD record
ord-22212e60a44f447ab5014d23f06f8f48
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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