Toluene → HCID 68431889, compound

HRID 2092113Notes

Reaction equation

HRID 2092113 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[OH:20])=[O:11])[N:5]=[CH:4][C:3]=1[NH:21][C@@H:22]1[CH2:27][C@@H:26]2[CH2:28][C@@H:24]([C:25]2([CH3:30])[CH3:29])[C@H:23]1[CH3:31].[CH3:32][CH:33](O)[CH3:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[O:20][CH:33]([CH3:34])[CH3:32])=[O:11])[N:5]=[CH:4][C:3]=1[NH:21][C@@H:22]1[CH2:27][C@@H:26]2[CH2:28][C@@H:24]([C:25]2([CH3:30])[CH3:29])[C@H:23]1[CH3:31]

Participants

7

Reactant 5

HCID 1140TolueneHCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68432036HCID 68432036, compound

Product 1

HCID 68431889HCID 68431889, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[5-Chloro-6-oxo-4-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-1(6H)-yl]-N-[(3-hydroxypyridin-4-yl)methyl]acetamide (26.6 mg, 0.06 mmol) in tetrahydrofuran (1 mL) was mixed with 2-propanol (10.9 mg, 0.18 mmol), triphenylphosphine (23.6 mg, 0.09 mmol) and diethyl azodicarboxylate in toluene (2.2 M, 0.04 mL, 0.09 mmol) at 0° C. and stirred at room temperature for 4 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (ethyl acetate/methanol 20/1) to give the desired product (4.48 mg, 15%).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel chromatography (ethyl acetate/methanol 20/1)

Sources & evidence

ORD record
ord-1f534f5f7d264804970707caad3a2cdf
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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