Pyridine → HCID 22179997, compound

HRID 1795957Notes

Reaction equation

HRID 1795957 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]([CH:21]1[CH2:23][CH2:22]1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:32])=O>C(Cl)Cl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]([Cl:32])[CH:21]1[CH2:23][CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22180051HCID 22180051, compound

Product 1

HCID 22179997HCID 22179997, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-benzyl-7-chloro-2-(cyclopropyl-hydroxy-methyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (1.40 g, 4.24 mmol) and pyridine (1.5 mL, 18.5 mmol) in CH2Cl2 (20 mL) was added thionyl chloride (2 M, 4.5 mL, 9.0 mmol) at 0° C. under nitrogen and stirred for 20 min. The reaction mixture was then stirred at rt overnight, poured into ice water, and extracted with CH2Cl2 (3×40 mL). The organic layers were washed with brine and dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1:9) gave the title compound as a white solid (0.96 g, 65%): 1H NMR (CDCl3) δ 7.22 (m, 3H), 7.04 (m, 3H), 6.48 (d, 1H, J=4.4 Hz), 6.05 (d, 1H, J=16.5 Hz), 4.68 (d, 1H, J=16.5 Hz), 3.81 (d, 1H, J=10.45 Hz), 1.96 (m, 1H), 1.19 (m, 1H), 0.72 (m, 1H), 0.57 (m, 1H), 0.22 (m, 1H), −0.35 (m, 1H); 3C NMR (CDCl3) δ 154.2, 148.2, 136.4, 129.2, 128.0, 125.8, 118.0, 117.6, 110.6, 109.0, 62.5, 44.1, 15.3, 7.22, 6.19; MS (ESI+) 348.02 (M++H), 370.01 (M++Na).

Workup

  1. stirringThe reaction mixture was then stirred at rt overnight
  2. extractionextracted with CH2Cl2 (3×40 mL)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1:9)

Sources & evidence

ORD record
ord-e8bbbff829af4fa4a5fc9d2fffc2a37a
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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