Hydrochloric Acid → HCID 11978434, compound

HRID 1670478Notes

Reaction equation

HRID 1670478 reaction equation
C(O[C:6](=O)[N:7](C)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:26]3[C:25]4[CH:24]=[C:23]([C:27]5[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=5)[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:16]([CH3:33])[C:15]2=[O:34])=[CH:10][CH:9]=1)(C)(C)C.Cl.N1C=CC=CC=1.[S:44](Cl)([CH3:47])(=[O:46])=[O:45]>O1CCOCC1.C(Cl)Cl>[CH3:6][N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:26]3[C:25]4[CH:24]=[C:23]([C:27]5[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=5)[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:16]([CH3:33])[C:15]2=[O:34])=[CH:10][CH:9]=1)[S:44]([CH3:47])(=[O:46])=[O:45]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 11978435HCID 11978435, compound

Product 1

HCID 11978434HCID 11978434, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

62 mg (0.128 mmol) of methyl-[4-(3-methyl-2-oxo-8-pyridin-3-yl-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-carbamic acid tert-butyl ester (Example 50a) is treated with 2.5 ml of 1 M HCl in dioxane at it for 1 h, and then the solution is evaporated to dryness. The residue is taken in 2 ml of CH2Cl2 together with 414 μl (5.13 mmol) of pyridine and 66 mg (0.579 mmol) of mesylchloride (Fluka, Buchs, Switzerland). The solution is stirred at it for 17.5 h, then 15 mg (0.129 mmol) of mesylchloride are added and the reaction mixture is stirred at rt for 5.5 h. The reaction is quenched with sat. aqueous NaHCO3 and extracted with CH2Cl2 (2×). The organic layers are washed with brine, dried over Na2SO4, filtered and evaporated. The residue is purified by preparative HPLC to give the title compound as a yellowish solid. ES-MS: 460 (M+H)+; analytical HPLC: tret=2.25 min (Grad 1).

Workup

  1. customthe solution is evaporated to dryness
  2. stirringthe reaction mixture is stirred at rt for 5.5 h
  3. customThe reaction is quenched with sat. aqueous NaHCO3
  4. extractionextracted with CH2Cl2 (2×)
  5. washThe organic layers are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-017b88a0f73e42758e2b540591a88178
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

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