Hydrochloric Acid → [3-Fluoro-4-(3-piperazin-1-yl-propoxy)-phenyl]-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone Dihydrochloride

HRID 220873Notes

Reaction equation

HRID 220873 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][O: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[F:41])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:42]>CO.O1CCOCC1>[ClH:42].[ClH:42].[F:41][C:19]1[CH:20]=[C:21]([C:24]([N:26]2[CH2:35][C:34]3[CH:33]=[N:32][N:31]([CH3:36])[C:30]=3[NH:29][C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[O:25])[CH:22]=[CH:23][C:18]=1[O:17][CH2:16][CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1361283664-{3-[2-Fluoro-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenoxy]-propyl}-piperazine-1-carboxylic Acid Tert-butyl Ester

Product 1

HCID 135736023[3-Fluoro-4-(3-piperazin-1-yl-propoxy)-phenyl]-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone DihydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-{3-[2-fluoro-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenoxy]-propyl}-piperazine-1-carboxylic acid tert-butyl ester from Example E49.1 (615 mg, 1.09 mmol) in methanol (2 ml) at 0° C. was treated with 4N HCl in dioxan (5 ml). The solution was allowed to warm to room temperature and stirred for 1 h. Solvents were removed in vacuo to give a white foam identified as the title compound (585 mg, 100%).

Workup

  1. customat 0° C.
  2. customSolvents were removed in vacuo
  3. customto give a white foam

Sources & evidence

ORD record
ord-d0815d787fcd433aa7937368f81b5dfe
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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