Hydrochloric Acid → 1-(4-Cyclopropylaminomethyl-piperidin-1-yl)-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propan-1-one

HRID 220937Notes

Reaction equation

HRID 220937 reaction equation
C(OC(=O)[N:7]([CH:43]1[CH2:45][CH2:44]1)[CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:42])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([N:26]3[CH2:35][C:34]4[CH:33]=[N:32][N:31]([CH3:36])[C:30]=4[NH:29][C:28]4[CH:37]=[CH:38][CH:39]=[CH:40][C:27]3=4)=[O:25])=[CH:20][C:19]=2[CH3:41])[CH2:11][CH2:10]1)(C)(C)C.Cl>CO.O1CCOCC1>[CH:43]1([NH:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:42])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]4[CH2:35][C:34]5[CH:33]=[N:32][N:31]([CH3:36])[C:30]=5[NH:29][C:28]5[CH:37]=[CH:38][CH:39]=[CH:40][C:27]4=5)=[O:25])=[CH:20][C:19]=3[CH3:41])[CH2:11][CH2:10]2)[CH2:44][CH2:45]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136128441Cyclopropyl-(1-{3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyl}-piperidin-4-ylmethyl)-carbamic Acid Tert-butyl Ester

Product 1

HCID 1357360631-(4-Cyclopropylaminomethyl-piperidin-1-yl)-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propan-1-oneYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Cyclopropyl-(1-{3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyl}-piperidin-4-ylmethyl)-carbamic acid tert-butyl ester from Example E86.3 (220 mg, 0.35 mmol) was dissolved in methanol (5 ml) and 4M HCl solution in dioxan (5 ml) was added. The mixture was stirred for 2 h at room temperature then concentrated in vacuo to give an off-white solid identified as the title compound (189 mg, 95%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customto give an off-white solid

Sources & evidence

ORD record
ord-a5bbe19892c14f3e8ffd391b922c2c56
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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