Chlorosuccinimide → HCID 86658562, compound

HRID 1520209Notes

Reaction equation

HRID 1520209 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:14]=[C:15]([NH:18][C:19]4[N:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[S:16][CH:17]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Cl:27]N1C(=O)CCC1=O>CN(C=O)C>[Cl:27][C:17]1[S:16][C:15]([NH:18][C:19]2[N:20]=[CH:21][CH:22]=[CH:23][N:24]=2)=[N:14][C:13]=1[C:11]1[CH:10]=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:26][CH:25]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86658563HCID 86658563, compound

Product 1

HCID 86658562HCID 86658562, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Scheme 7, Step 1: To a solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(pyrimidin-2-yl)thiazol-2-amine (0.85 mmol, 0.31 g) in DMF (1 mL) was added 1-chloropyrrolidine-2,5-dione (0.64 mmol, 85 mg). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated aqueous solution of Na2CO3 and extracted with AcOEt. The combined organic layers were dried over MgSO4, were filtered and were evaporated under reduced pressure to afford 5-chloro-4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-N-(pyrimidin-2-yl)thiazol-2-amine (0.33 mmol, 130 mg, 38%) as an orange solid.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of Na2CO3
  2. extractionextracted with AcOEt
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationwere filtered
  5. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-b28c6d990e464208a1689a32ed1b43fa
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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