Hydrochloric Acid → HCID 86681957, compound

HRID 1749759Notes

Reaction equation

HRID 1749759 reaction equation
C(O[C:6]([N:8]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][CH:17]=[C:16]2/[CH:20]=[C:21]1\[O:22][C:23]2[C:30]([CH2:31][N:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[C:29]([OH:45])[CH:28]=[CH:27][C:24]=2[C:25]\1=[O:26])C)=O)(C)(C)C.[ClH:46]>C(Cl)Cl.O1CCOCC1>[ClH:46].[ClH:46].[ClH:46].[OH:45][C:29]1[CH:28]=[CH:27][C:24]2[C:25](=[O:26])/[C:21](=[CH:20]/[C:16]3[C:15]4[C:19](=[C:11]([CH2:10][NH:8][CH3:6])[CH:12]=[CH:13][CH:14]=4)[NH:18][CH:17]=3)/[O:22][C:23]=2[C:30]=1[CH2:31][N:32]1[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681955HCID 86681955, compound

Product 1

HCID 86681957HCID 86681957, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(7-{[tert-butoxycarbonyl(methyl)-amino]methyl}-1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.044 g, 0.071 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 4 hours. The mixture was azeotroped twice with toluene under reduced pressure, and then the residual solid was suspended in a mixed solvent of chloroform and methanol and thereby washed to obtain (Z)-6-hydroxy-2-({7-[(methylamino)methyl]-1H-indol-3-yl}methylene)-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one trihydrochloride (0.025 g, 72%).

Workup

  1. customThe mixture was azeotroped twice with toluene under reduced pressure
  2. washwashed

Sources & evidence

ORD record
ord-92d49cc0f2c04ec28783d311ec47f332
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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