Ethyl benzoylformate → HCID 178517175, compound

HRID 2064453Notes

Reaction equation

HRID 2064453 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.O=[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](OCC)=[O:13].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:7]=1)=[N:8][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[C:12]([OH:13])[N:9]=2

Participants

5

Reactant 3

HCID 15349Ethyl benzoylformateHCID 81531DiisopropylethylamineHCID 106306156-Chloropyridine-2,3-diamine

Product 1

HCID 178517175HCID 178517175, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-chloropyridine-2,3-diamine (8-1, Oguchi, et. al. J. Med. Chem. (2000), 43, 3052-3066; 15 g, 105 mmol) in DMF (53 mL) was added ethyl oxo(phenyl)acetate (23 mL, 160 mmol) and DIPEA (37 ml, 210 mmol). After 72 hours, the reaction was concentrated to dryness. The resulting material was suspended in ethyl acetate/water and filtered to give 8-2 as a solid. The organic phase was washed with water, NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated. The crude mixture was suspended in DCM (200 mL) and filtered to give another batch of 8-2 as a solid. MS calculated: 257.7; observed: 258.0.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. filtrationfiltered

Sources & evidence

ORD record
ord-67d05fb910a94b86b08c624856295417
Source dataset
uspto-grants-2012_10
Patent number
US08288407B2

Reaction notes

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