Oxalyl chloride → HCID 67287755, compound

HRID 1626483Notes

Reaction equation

HRID 1626483 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[S:35][C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:37][N:38]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18](=[O:20])[NH:33][C:34]3[S:35][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:37][N:38]=3)=[CH:21][CH:22]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:23]([O:25][CH3:26])=[O:24])#[N:2]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2194082-Amino-5-phenyl-1,3,4-thiadiazoleHCID 462211084-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid

Product 1

HCID 67287755HCID 67287755, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (20 mg, 0.057 mmol) was diluted with DCM (1 ml) followed by the addition of oxalyl chloride in DCM (2M) (31 μl, 0.062 mmol) and DMF (1 drop). After stirring for 15 minutes, 2-amino-5-phenyl-[1,3,4]-thiadiazole (10 mg, 0.057 mmol) and DIEA (25 μl, 0.14 mmol) were added. After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 6-cyano-7-(4-(5-phenyl-1,3,4-thiadiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (17 mg, 0.033 mmol, 59% yield).

Workup

  1. stirringAfter stirring for 12 hours
  2. washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record
ord-73d1fb3b67b443c4a057d7d741acd9fa
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…