Chlorosuccinimide → 3-(4-Chloro-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660753Notes

Reaction equation

HRID 1660753 reaction equation
[CH2:1]([CH:3]([C:6]1[N:11]2[N:12]=[C:13]([CH3:26])[C:14]([C:15]3[S:19][C:18]([C:20]4[N:21]([CH3:25])[N:22]=[CH:23][N:24]=4)=[N:17][CH:16]=3)=[C:10]2[N:9]=[C:8]([CH3:27])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[Cl:28]N1C(=O)CCC1=O>ClCCl.C(#N)C>[Cl:28][C:16]1[N:17]=[C:18]([C:20]2[N:21]([CH3:25])[N:22]=[CH:23][N:24]=2)[S:19][C:15]=1[C:14]1[C:13]([CH3:26])=[N:12][N:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][C:8]([CH3:27])=[N:9][C:10]=12

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 674282857-(1-ethyl-propyl)-2,5-dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 674293153-(4-Chloro-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineYield 74%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 7-(1-ethyl-propyl)-2,5-dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl)-pyrazolo[1,5-a]pyrimidine (20 mg, 0.052 mmol) and N-chlorosuccinimide (7.6 mg, 0.0569 mmol) in dichloromethane (0.5 mL) and acetonitrile (0.5 mL) at room temperature overnight in a vial. Concentrate to a residue. Purify by flash chromatography, eluting with hexanes and then with hexanes/ethyl acetate (10/1.5) to give the title compound (16 mg). ES/MS m/z (35Cl) 416.0 (M+1)+.

Workup

  1. concentrationConcentrate to a residue
  2. customPurify by flash chromatography
  3. washeluting with hexanes

Sources & evidence

ORD record
ord-a0b918483ede4098952cd2c2cd286a73
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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