Hydrogen Bromide → 2-(2-Amino-thiazol-4-yl)-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone trihydrobromide

HRID 901027Notes

Reaction equation

HRID 901027 reaction equation
C(OC(=O)[NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])[N:12]=1)(C)(C)C.[BrH:30]>C(O)(=O)C.CCOCC>[BrH:30].[BrH:30].[BrH:30].[NH2:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([N:16]2[CH2:17][CH2:18][N:19]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[CH2:20][CH2:21]2)=[O:15])[N:12]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 59698869(4-{2-[4-(1-Methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 866060022-(2-Amino-thiazol-4-yl)-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone trihydrobromide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

47.2 To a stirred suspension of 3.9 g (4-{2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-carbamic acid tert-butyl ester was added 40 ml of 33% HBr in acetic acid. The reaction mixture was stirred at r.t. for 4 h. The mixture was left overnight in the fridge. Then it was concentrated to leave an off-white solid which was suspended in 50 ml Et2O, triturated and stirred at r.t. for 3 h. The product was collected by filtration, washed with Et2O and dried to give 5.6 g 2-(2-amino-thiazol-4-yl)-1-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-ethanone trihydrobromide. Off-white solid. MS 324.4 ([M+H]+)

Workup

  1. waitThe mixture was left overnight in the fridge
  2. concentrationThen it was concentrated
  3. customto leave an off-white solid which
  4. customtriturated
  5. stirringstirred at r.t. for 3 h
  6. filtrationThe product was collected by filtration
  7. washwashed with Et2O
  8. customdried

Sources & evidence

ORD record
ord-30c1679e95d24b9897ef17378014617c
Source dataset
uspto-grants-2008_04
Patent number
US07361672B2

Reaction notes

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