Hydrochloric Acid → Hydrochloric Acid

HRID 888005Notes

Reaction equation

HRID 888005 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.[ClH:30]>O1CCOCC1>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[CH:19][CH:18]=1.[ClH:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59830876HCID 59830876, compound

Product 2

HCID 313Hydrochloric AcidYield 46%HCID 9795987HCID 9795987, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-4-pyridin-4-ylbenzamide (Method 1; 100 mg, 0.26 mmol), 1,4-dioxane (2 ml) and a 4M solution of hydrogen chloride in dioxane (2 ml) were stirred at ambient temperature for approximately 20 hours. The resultant precipitate was collected by filtration and washed with iso-hexane and diethyl ether and dried in vacuo to give the title compound as its hydrochloride (43 mg, 46%); NMR Spectrum: (DMSO-d6) 7.31 (m, 2H), 7.39 (t, 1H), 7.54 (t, 1H), 8.17 (d, 2H), 8.30 (d, 2H), 8.40 (d, 2H), 8.96 (d, 2H), 10.62 (s, 1H); Mass Spectrum: M+H+ 290.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with iso-hexane and diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1c65351d692b4cc0a93199ce5474603b
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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