Pyridine → N-(6-Bromo-1-methyl-1H-indazol-4-yl)-2-(chloromethyl)-4-thiazolecarboxamide

HRID 244716Notes

Reaction equation

HRID 244716 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.N1C=CC=CC=1.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]([Cl:28])=O)[S:24][CH:25]=1.C(=O)(O)[O-:30].[Na+]>ClCCl.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([NH:12][C:20]([C:21]2[N:22]=[C:23]([CH2:26][Cl:28])[S:24][CH:25]=2)=[O:30])[CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 106079144-(chloromethyl)-1,3-thiazole-2-carbonyl ChlorideHCID 58255771HCID 58255771, compound

Product 1

HCID 58255850N-(6-Bromo-1-methyl-1H-indazol-4-yl)-2-(chloromethyl)-4-thiazolecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

6-Bromo-1-methyl-1H-indazol-4-amine (1 g, 4.42 mmol) was dissolved in dichloromethane (DCM) (10 mL) and pyridine (0.429 mL, 5.31 mmol) added. The mixture was cooled to 0° C. in an ice-water bath and 4-(chloromethyl)-1,3-thiazole-2-carbonyl chloride (0.867 g, 4.42 mmol) in DCM (10 ml) was added portionwise over 5 mins. The mixture was stirred for 2 hours and allowed to warm to room temperature. Saturated sodium bicarbonate solution (15 ml) was added and the mixture stirred vigorously for 10 mins. The mixture was diluted with water (50 ml) and DCM (50 ml), but a precipitate was still present. This was collected by filtration, washed with DCM and air dried to afford the title compound as a yellow/brown solid (860 mg).

Workup

  1. temperatureto warm to room temperature
  2. stirringthe mixture stirred vigorously for 10 mins
  3. filtrationThis was collected by filtration
  4. washwashed with DCM and air
  5. customdried

Sources & evidence

ORD record
ord-6777d20b6c0948dfb31836ffe213e667
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

Loading…