Thionyl Chloride → methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate hydrochloride

HRID 1471758Notes

Reaction equation

HRID 1471758 reaction equation
O[CH2:2][C:3]1[C:4]([C:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)[Cl:22]>C(Cl)Cl>[ClH:22].[Cl:22][CH2:2][C:3]1[C:4]([C:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:10]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86690795methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

Product 1

HCID 86690796methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate (51 mg, 0.20 mmol) in DCM (5 mL) was added SOCl2 (1.0 mL) at rt. The reaction mixture was stirred at rt for 4 h and concentrated to dryness. The crude solid was suspended in toluene and concentrated to dryness. The process was repeated three times and dried under vacuum to give methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate hydrochloride (63 mg) as an off-white solid, which was used for next step without further purification.

Workup

  1. concentrationconcentrated to dryness
  2. concentrationconcentrated to dryness
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5993a152c5994bd69bf196bda70a6dd2
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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