Hydrochloric Acid → HCID 67365116, compound

HRID 524219Notes

Reaction equation

HRID 524219 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].[F:26][C:27]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][O:38][CH3:39])=[CH:32][C:28]=1[C:29](O)=[O:30].C1C=CC2N(O)N=NC=2C=1.Cl>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:12]2[C:13]([CH3:25])([CH3:24])[C:14](=[O:23])[N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:29]([C:28]4[CH:32]=[C:33]([O:36][CH2:37][O:38][CH3:39])[CH:34]=[CH:35][C:27]=4[F:26])=[O:30])[CH2:19][CH2:18]3)[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 11790202HCID 11790202, compoundHCID 666164065-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-piperidin-4-yl-2,4-dihydro-3H-pyrazol-3-one hydrochloride2×

Product 1

HCID 67365116HCID 67365116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.5 g 5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2-(piperidin-4-yl)-2,4-dihydro-3H-pyrazol-3-one hydrochloride (compound B1*HCl) in 60 ml of DCM a solution of 2.4 g 2-fluoro-5-(methoxymethoxy)benzoic acid 20 ml of DCM, 1.7 ml TEA, 1.7 g HOBt and 2.4 g EDCi*HCl are added. The reaction mixture is stirred for 90 min until the reaction is complete according to TLC analysis. The reaction mixture is quenched with 1 M aqueous hydrochloric acid, the phases are separated and the organic phase is washed with 1 M aqueous hydrochloric acid again, with water, twice with 1M aqueous sodium carbonate solution and with brine. The organic phase is dried over MgSO4, and the solvent is removed under reduced pressure resulting in a crude product, which is purified by crystallization from diethyl ether to yield 5-(3,4-dimethoxyphenyl)-2-(1-{[2-fluoro-5-(methoxymethoxy)phenyl]carbonyl}piperidin-4-yl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one as the product.

Workup

  1. customThe reaction mixture is quenched with 1 M aqueous hydrochloric acid
  2. customthe phases are separated
  3. washthe organic phase is washed with 1 M aqueous hydrochloric acid again
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent is removed under reduced pressure
  6. customresulting in a crude product, which
  7. customis purified by crystallization from diethyl ether

Sources & evidence

ORD record
ord-c35a044613bb4a3c9a60476d965cc9e6
Source dataset
uspto-grants-2016_05
Patent number
US09340522B2

Reaction notes

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