Hydrochloric Acid → (S)-1-Cyclobutyl 3-(4-(2-methylpiperazine-1-carbonyl)phenyl)urea hydrochloride

HRID 1878379Notes

Reaction equation

HRID 1878379 reaction equation
[CH:1]1([NH:5][C:6](=[O:30])[NH:7][C:8]2[CH:29]=[CH:28][C:11]([C:12]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH:15]3[CH3:27])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[ClH:31]>>[ClH:31].[CH:1]1([NH:5][C:6]([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]3[CH3:27])=[O:13])=[CH:28][CH:29]=2)=[O:30])[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 70806790tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 66878377(S)-1-Cyclobutyl 3-(4-(2-methylpiperazine-1-carbonyl)phenyl)urea hydrochloride

Procedure

tert-Butyl 4-(4-(3-cyclobutylureido)benzoyl)-3-methylpiperazine-1-carboxylate (0.20 g, 0.48 mmol) was treated with an ethanolic solution of hydrochloric acid (2 mL, 14.5 wt % hydrochloric acid in ethanol). The resultant mixture was stirred at room temperature for 2 hours. The mixture was concentrated under vacuum, azeotroped with dichloromethane (×2) and dried under vacuum to afford the title compound (0.152 g) as a white foamy solid. MS (ESI) m/z 317.0 [M+H]+

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customazeotroped with dichloromethane (×2)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c1e42594b00b40019a56b1d60571926d
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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