Hydrochloric Acid → HCID 178520218, compound

HRID 2383437Notes

Reaction equation

HRID 2383437 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15](=[O:36])[CH:16]([N:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.[ClH:37]>ClCCl.O1CCOCC1>[Cl-:37].[Br:1][C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15](=[O:36])[CH:16]([N:23]4[CH2:24][CH2:25][NH2+:26][CH2:27][CH2:28]4)[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178452336HCID 178452336, compound

Product 1

HCID 178520218HCID 178520218, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethyl)piperazine-1-carboxylate (0.075 g, 0.17 mmol) in dichloromethane (12 mL) and 1,4-dioxane (6 mL) was added a 4 M solution of HCl gas in 1,4-dioxane (0.82 mL, 3.4 mmol). The reaction was shaken at room temperature for 16 hours. During the reaction a pale tan solid precipitate was formed. The solvent was removed under reduced pressure to give the pure desired product, 4-(2-(1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethyl)piperazin-1-ium chloride (0.064 g, 71%) as an tan solid. M.p.>245° C.; 1H NMR (400 MHz, DMSO-d6) δ13.98 (s, 1H), 9.92 (brs, 2H), 8.44/8.21 (s, 1H, rotamers), 7.44-7.68 (m, 5H), 6.28 (m, 1H), 4.75-4.92 (m, 2H), 4.11 (m, 8H), 3.90 (m, 1H), 3.66 (m, 1H), 3.29 (m, 1H), 2.62 (m, 1H); LCMS [M+H]: 455.

Workup

  1. customDuring the reaction a pale tan solid precipitate
  2. customwas formed
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eb7dcc590af54a9bbc7a2254854b7070
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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