Oxalyl chloride → HCID 67288212, compound

HRID 1626477Notes

Reaction equation

HRID 1626477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(Cl)(=O)C(Cl)=O.[Cl:33][C:34]1[C:35]([CH2:41][CH2:42][NH2:43])=[N:36][CH:37]=[C:38]([Cl:40])[CH:39]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17](=[O:18])[NH:43][CH2:42][CH2:41][C:35]3[C:34]([Cl:33])=[CH:39][C:38]([Cl:40])=[CH:37][N:36]=3)=[CH:20][CH:21]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 230682892-(3,5-Dichloropyridin-2-yl)ethan-1-amineHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Product 1

HCID 67288212HCID 67288212, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 60 mg, 0.16 mmol) was diluted with DCM (1 mL) followed by the addition of oxalyl chloride in DCM (2M) (88 μl, 0.18 mmol) and DMF (1 drop). After stirring for 10 minutes, 2-(3,5-dichloropyridin-2-yl)ethanamine (30 mg, 0.16 mmol) and DIEA (111 μl, 0.64 mmol) were added. The reaction was stirred for 2 hours. The reaction was loaded onto silica gel and eluted with a gradient of 5%-75% ethyl acetate/hexanes to yield the desired compound (40 mg, 0.073 mmol, 46% yield).

Workup

  1. stirringThe reaction was stirred for 2 hours
  2. washeluted with a gradient of 5%-75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fb63532bc6604333905b2e81b47ff742
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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