Hydrochloric Acid → 4-(2-Amino-7-ethoxy-6-phenoxy-quinolin-3-yl)-N-(3,3-dimethyl-butyl)-4-(tetrahydro-pyran-4-yl)-butyramide hydrochloride

HRID 252471Notes

Reaction equation

HRID 252471 reaction equation
[CH3:1][C:2]([CH3:41])([CH3:40])[CH2:3][CH2:4][NH:5][C:6](=[O:39])[CH2:7][CH2:8][CH:9]([CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:10]([C:31]#[N:32])=[CH:11][C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:25][CH2:26][CH3:27])=[CH:14][C:13]=1[N+:28]([O-])=O.[NH4+].[Cl-:43].Cl>CO.[Zn]>[ClH:43].[NH2:32][C:31]1[C:10]([CH:9]([CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH2:8][CH2:7][C:6]([NH:5][CH2:4][CH2:3][C:2]([CH3:41])([CH3:40])[CH3:1])=[O:39])=[CH:11][C:12]2[C:13](=[CH:14][C:15]([O:25][CH2:26][CH3:27])=[C:16]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)[N:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 672691075-Cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (3,3-dimethyl-butyl)-amide

Product 1

HCID 672695114-(2-Amino-7-ethoxy-6-phenoxy-quinolin-3-yl)-N-(3,3-dimethyl-butyl)-4-(tetrahydro-pyran-4-yl)-butyramide hydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-cyano-6-(4-ethoxy-2-nitro-5-phenoxy-phenyl)-4-(tetrahydro-pyran-4-yl)-hex-5-enoic acid (3,3-dimethyl-butyl)-amide (160 mg, 0.28 mmol) in methanol was added Zn (0.4 g) and NH4Cl (0.10 g). The resulting mixture was treated under μW at 95° C. for 20 min, filtered through Celite® and concentrated. The resulting crude product was purified by chromatography (silica gel, 0-2% methanol in methylene chloride) to yield a white solid that was converted to the HCl salt of the title compound by reacting with 1M HCl in diethyl ether.

Workup

  1. additionThe resulting mixture was treated under μW at 95° C. for 20 min
  2. filtrationfiltered through Celite®
  3. concentrationconcentrated
  4. customThe resulting crude product was purified by chromatography (silica gel, 0-2% methanol in methylene chloride)
  5. customto yield a white solid

Sources & evidence

ORD record
ord-fa171346fe3446d4b05bd4cecc1c2d29
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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