Diethyl Oxalate → HCID 67112029, compound

HRID 1177540Notes

Reaction equation

HRID 1177540 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH2:28])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[C:29](OCC)(=[O:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1(C)C=CC=CC=1.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][NH:28][C:29](=[O:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

5

Reactant 2

HCID 7268Diethyl OxalateHCID 57397896HCID 57397896, compound

Product 1

HCID 67112029HCID 67112029, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

2-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-ethanamine (112 mg, 0.29 mmol) was dissolved in toluene (2.9 mL) before diethyl oxalate (0.39 mL, 2.88 mmol) was added and stirred at 110° C. for 16 h. The reaction mixture was diluted with 75 mL of DCM, added to a separatory funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give ethyl 2-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)ethylamino)-2-oxoacetate after flash chromatography. MS (ESI) m/z: Calculated: 489.2; Observed: 490.4 (M++H).

Workup

  1. additionwas added
  2. additionadded to a separatory funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washwashed with sodium bicarbonate (saturated, aqueous)
  5. customseparated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap

Sources & evidence

ORD record
ord-e0108eccf6564c388b1dacc732d6b82d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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