Thionyl Chloride → 3'-(4-chloromethyl-phenyl)-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

HRID 220567Notes

Reaction equation

HRID 220567 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:20]([C:21]4[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=4)=[N:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[CH:4]=[N:3]1.S(Cl)([Cl:31])=O>C(Cl)Cl>[ClH:31].[ClH:31].[Cl:31][CH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[C:15]([N:12]3[CH2:13][CH2:14][N:9]([CH2:8][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:6]=4[CH3:7])[CH2:10][CH2:11]3)=[N:16][CH:17]=[CH:18][N:19]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59321924{4-[4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-methanol

Product 1

HCID 685941603'-(4-chloromethyl-phenyl)-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve {4-[4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl]-phenyl}-methanol (1.00 g, 2.64 mmol) in DCM (60 mL). Add thionyl chloride (6 mL) and stir at room temperature for 2 hr. Concentrate in vacuo to give 3′-(4-chloromethyl-phenyl)-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride as a yellow solid (1.20 g, 100%). MS (ES): m/z=397 [M+H]+

Workup

  1. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-11b37ea7920a4c4686c73b7c6db923d6
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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