Hydrochloric Acid → N-Cyclopropyl-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-N-piperidin-4-ylmethyl-propionamide Hydrochloride

HRID 220939Notes

Reaction equation

HRID 220939 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH:44]2[CH2:46][CH2:45]2)[C:16](=[O:43])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([N:27]3[CH2:36][C:35]4[CH:34]=[N:33][N:32]([CH3:37])[C:31]=4[NH:30][C:29]4[CH:38]=[CH:39][CH:40]=[CH:41][C:28]3=4)=[O:26])=[CH:21][C:20]=2[CH3:42])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:47]>O1CCOCC1>[ClH:47].[CH:44]1([N:15]([CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:16](=[O:43])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([N:27]3[CH2:36][C:35]4[CH:34]=[N:33][N:32]([CH3:37])[C:31]=4[NH:30][C:29]4[CH:38]=[CH:39][CH:40]=[CH:41][C:28]3=4)=[O:26])=[CH:21][C:20]=2[CH3:42])[CH2:45][CH2:46]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1361283784-[(Cyclopropyl-{3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyl}-amino)-methyl]-piperidine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 136346642N-Cyclopropyl-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-N-piperidin-4-ylmethyl-propionamide HydrochlorideYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[(Cyclopropyl-{3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyl}-amino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester from Example E87.1 (235 mg, 0.37 mmol) was dissolved in 4M HCl solution in dioxan (5 ml). The mixture was stirred for 1 h at room temperature, concentrated in vacuo and azeotroped with toluene. The residue was dissolved in 1M HCl, washed twice with dichloromethane and freeze-dried to give an off-white solid identified as the title compound (82 mg, 39%).

Workup

  1. concentrationconcentrated in vacuo
  2. customazeotroped with toluene
  3. dissolutionThe residue was dissolved in 1M HCl
  4. washwashed twice with dichloromethane
  5. customfreeze-dried
  6. customto give an off-white solid

Sources & evidence

ORD record
ord-4e3d0ca7c1db44efbe83e73a40006256
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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