Dichloromethane → 1-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)-3-(pyrrolidin-3-yl)urea hydrochloride

HRID 68683Notes

Reaction equation

HRID 68683 reaction equation
[CH3:1][S:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:27])[NH:14][CH:15]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)=[CH:9][CH:10]=2)[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:4]=1.[Cl:34]CCl>>[ClH:34].[CH3:1][S:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]([NH:14][CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)=[O:27])=[CH:9][CH:10]=2)[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:4]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67448228tert-butyl 3-(3-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)ureido)pyrrolidine-1-carboxylate

Product 1

HCID 674494631-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)-3-(pyrrolidin-3-yl)urea hydrochloride

Conditions

Temperature
0 °C

Procedure

Into a 50-mL 3-necked round-bottom flask, was placed a solution of tert-butyl 3-(3-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)ureido)pyrrolidine-1-carboxylate (120 mg, 0.26 mmol, 1.00 equiv) in dichloromethane (4 mL). The solution was bubbled with HCl (g) at 0° C. in 30 min. The resulting solution was stirred for 30 min at 0° C. The solids were collected by filtration. The solid was washed with ethyl acetate/methanol (2×3.8 mL) to yield 1-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)-3-(pyrrolidin-3-yl)urea hydrochloride as a white solid.

Workup

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. customThe solution was bubbled with HCl (g) at 0° C. in 30 min
  3. filtrationThe solids were collected by filtration
  4. washThe solid was washed with ethyl acetate/methanol (2×3.8 mL)

Sources & evidence

ORD record
ord-f9d9241aa2464d079463c614c92d25e2
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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