Oxalyl chloride → HCID 67287686, compound

HRID 1626471Notes

Reaction equation

HRID 1626471 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[CH:35]=[C:36]([C:40]2[N:45]=[CH:44][C:43]([NH2:46])=[CH:42][N:41]=2)[CH:37]=[CH:38][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:21]=[CH:20][C:16]([C:17](=[O:18])[NH:46][C:43]3[CH:44]=[N:45][C:40]([C:36]4[CH:37]=[CH:38][CH:39]=[C:34]([Cl:33])[CH:35]=4)=[N:41][CH:42]=3)=[CH:15][CH:14]=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 431422892-(3-Chlorophenyl)-5-pyrimidinamineHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Product 1

HCID 67287686HCID 67287686, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 45 mg, 0.12 mmol) was diluted with DCM (1 mL) followed by the addition of oxalyl chloride in DCM (2M) (66 μl, 0.13 mmol) and DMF (1 drop). 2-(3-chlorophenyl)pyrimidin-5-amine (25 mg, 0.12 mmol) and DIEA (52 μl, 0.30 mmol) were added and the reaction was stirred at ambient temperature for 4 hours. The reaction was loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes to yield the desired compound (45 mg, 0.080 mmol, 67% yield).

Workup

  1. washeluted with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a43d088181cc4121b3a7f72f38d20457
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…