Ethoxalyl chloride → HCID 46213116, compound

HRID 1632038Notes

Reaction equation

HRID 1632038 reaction equation
C(O[C:4](=[O:30])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[C:15]([F:29])=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:9][N:8]=1)C.ClC(=O)[C:33]([O:35][CH2:36][CH3:37])=[O:34]>ClCCl>[CH2:36]([O:35][C:33](=[O:34])[C:4]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[C:15]([F:29])=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:9][N:8]=1)=[O:30])[CH3:37]

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 58020092HCID 58020092, compound

Product 1

HCID 46213116HCID 46213116, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 20 mL vial was added [5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-ylmethyl]-carbamic acid ethyl ester (P-367) (152 mg, 0.43 mmol), dichloromethane (4 mL), TEA (0.11 mL, 0.85 mmol). The solution was cooled to 0° C. and Ethyl chlorooxoacetate (71 uL, 0.64 mmol) was added. After 20 minutes at room temperature, the organic solution was washed with H2O and brine, and then concentrated. Ethyl acetate was added to the residue, which produced a solid and was filtered. The solid was triturated with ether and dried to give N-[5-(3′-chloro-2-fluoro-6-methoxy-biphenyl-3-ylmethyl)-pyridin-2-ylmethyl]-oxalamic acid ethyl ester (I-40) (69 mg, 35%) as a gray-blue solid.

Workup

  1. washthe organic solution was washed with H2O and brine
  2. concentrationconcentrated
  3. additionEthyl acetate was added to the residue, which
  4. customproduced a solid
  5. filtrationwas filtered
  6. customThe solid was triturated with ether
  7. customdried

Sources & evidence

ORD record
ord-ee4523aa1c25467daa51f35f1e16107d
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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