Phosphorus oxychloride → HCID 22612066, compound

HRID 844049Notes

Reaction equation

HRID 844049 reaction equation
O[CH2:2][C:3]1([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[O:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([O:16][C:11]2[C:10]([C:9]3[O:23][CH2:2][C:3]4([CH2:4][CH2:5][CH2:6][CH2:7]4)[N:8]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22612316HCID 22612316, compound

Product 1

HCID 22612066HCID 22612066, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-(1-Hydroxymethyl-cyclopentyl)-2-(pyridin-3-yloxy)-nicotinamide (0.045 grams, 0.144 mmole) and phosphorus oxychloride in toluene (5 ml) was stirred over night. The mixture was concentrated to dryness and dissolved in methanol (5 ml) and potassium carbonate was added. The mixture was concentrated to give a crude product that was purified by chromatography on silica gel eluting with ethyl acetate to give a yellow oil (0.021 g). HRMS 296.1417; 1H NMR (400 mhz, CDCl3) d 1.65-1.74 (m, 4H), 1.86-1.91 (m, 2H), 1.96-2.03 (m, 2H), 4.25 (s, 2H), 7.08 (dd, J=7.5 Hz, 5.0 Hz, 1H), 7.32 (dd, J=8.3 Hz, 4.8 Hz, 1H), 7.51-7.54 (m, 1H), 8.15-8.22 (m, 2H), 8.43-8.50 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutiondissolved in methanol (5 ml)
  3. additionpotassium carbonate was added
  4. concentrationThe mixture was concentrated
  5. customto give a crude product that
  6. customwas purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-5b10e80637654dcdb3f21f9ae7f51722
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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