Oxalyl chloride → HCID 86608622, compound

HRID 1925339Notes

Reaction equation

HRID 1925339 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([OH:23])=O)=[CH:16][CH:15]=[CH:14]3)=[N:3][CH:2]=1.C(Cl)(C([Cl:28])=O)=O>C(Cl)Cl.CN(C=O)C>[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[C:4]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([C:21]([Cl:28])=[O:23])=[CH:16][CH:15]=[CH:14]3)=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 24822774HCID 24822774, compound

Product 1

HCID 86608622HCID 86608622, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-1-naphthoic acid (357 mg, 1.17 mmol) in DCM (11.7 mL) under an N2 atmosphere, was added DMF (2 drops) followed by (COCl)2 (143 μL, 1.64 mmol) dropwise. After stirring at RT for 4 hours, the reaction mixture became a yellow slurry. An aliquot was removed and placed in a vial containing 500 μl of 1M MeNH2. After 5 min, the resulting solution was analyzed by LCMS to indicate complete conversion to the methylamine and that no acid was present in the reaction mixture. The slurry was concentrated to a yellow stable solid, which was taken directly to the next step of the reaction sequence.

Workup

  1. customAn aliquot was removed
  2. additiona vial containing 500 μl of 1M MeNH2
  3. waitAfter 5 min
  4. concentrationThe slurry was concentrated to a yellow stable solid, which

Sources & evidence

ORD record
ord-2097809c91b64b6295ac22ec94d11eef
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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