Methanol → HCID 57896698, compound

HRID 2421892Notes

Reaction equation

HRID 2421892 reaction equation
[N:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:26])=O.CN(C=O)C.CO>ClCCCl>[N:1]1([S:7]([N:10]2[CH2:15][CH2:14][O:13][C:12]3[N:16]=[CH:17][C:18]([C:20]([Cl:26])=[O:22])=[CH:19][C:11]2=3)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57896688HCID 57896688, compound

Product 1

HCID 57896698HCID 57896698, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1-(piperidin-1-ylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylic acid (110 mg, 0.336 mmol) in DCE (5 mL) was added oxalyl chloride (293 μL, 3.36 mmol) and DMF (5 μL, 0.065 mmol). The reaction was heated to 50° C. and stirred at that temperature for 16 h. The reaction was concentrated in vacuo and used without further purification. The reaction yield was assumed to be 100% for calculation purposes only. LCMS (methanol adduct, i.e. the methyl ester; +ESI) m/z=342.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customused without further purification
  3. customThe reaction yield

Sources & evidence

ORD record
ord-34c821c330a6416b8ea03ed65691368d
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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