Oxalyl chloride → HCID 67287730, compound

HRID 1626393Notes

Reaction equation

HRID 1626393 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2].C(Cl)(=O)C(Cl)=O.[NH2:33][C:34]1[CH:35]=[N:36][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:38][CH:39]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C>[F:43][C:40]([F:41])([F:42])[C:37]1[N:36]=[CH:35][C:34]([NH:33][C:18]([C:17]2[CH:21]=[CH:22][C:14]([O:13][C:12]3[CH:11]=[C:10]4[C:5]([CH:6]([C:23]([O:25][CH3:26])=[O:24])[CH2:7][CH2:8][O:9]4)=[CH:4][C:3]=3[C:1]#[N:2])=[CH:15][CH:16]=2)=[O:20])=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27377445-Amino-2-(trifluoromethyl)pyridineHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

Product 1

HCID 67287730HCID 67287730, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (100 mg, 0.283 mmol) was diluted with dichloromethane (1 mL) followed by the addition of oxalyl chloride in dichloromethane (2M) (0.156 mL, 0.311 mmol) and 1 drop of DMF. After stirring for 10 minutes, 3-amino-6-(trifluoromethyl)pyridine (91.8 mg, 0.566 mmol) and diisopropylethylamine (0.123 mL, 0.708 mmol) were added and the reaction was stirred for 5 hours. The reaction was loaded onto a biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to provide the desired product (141 mg, 100% yield).

Workup

  1. stirringthe reaction was stirred for 5 hours
  2. washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record
ord-b4e3fb630a6c4c8a99a655ffded9a6e6
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…