1-Chloro-N,N-2-trimethylpropenylamine → 4-(4-Chlorophenyl)-5-(1,6-dihydro-1-methyl-6-oxo-3-pyridinyl)-4,5-dihydro-2-[(4-methoxyphenyl)methyl]-3-methylpyrrolo[3,4-c]pyrazol-6(2H)-one

HRID 873790Notes

Reaction equation

HRID 873790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:27][C:28]2[CH:33]=[CH:32][C:31](=[O:34])[N:30]([CH3:35])[CH:29]=2)[C:9]2[C:10]([C:24]([OH:26])=O)=[N:11][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:13]=2[CH3:14])=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9]3[C:10](=[N:11][N:12]([CH2:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[C:13]=3[CH3:14])[C:24](=[O:26])[N:27]2[C:28]2[CH:33]=[CH:32][C:31](=[O:34])[N:30]([CH3:35])[CH:29]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 1177027904-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 918262984-(4-Chlorophenyl)-5-(1,6-dihydro-1-methyl-6-oxo-3-pyridinyl)-4,5-dihydro-2-[(4-methoxyphenyl)methyl]-3-methylpyrrolo[3,4-c]pyrazol-6(2H)-oneYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylic acid (Step 1.5) (125 mg, 0.254 mmol) in CH2Cl2 (2 mL) under Ar was added 1-chloro-N,N,2-trimethyl-1-propenylamine (0.047 mL, 0.355 mmol) at 0° C. The reaction mixture was stirred for 1 hr at 0° C., quenched with a saturated aqueous solution of NaHCO3 (75 mL), and extracted with CH2Cl2. The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried over Na2SO4 the solvent was and evaporated off under reduced pressure. The crude residue was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-3.5%) to afford the title product (92 mg, 0.194 mmol, 76% yield) as a greenish solid. tR: 4.32 min (HPLC 1); tR: 0.97 min (LC-MS 2); ESI-MS: 475 [M+H]+ (LC-MS 2); Rf=0.65 (CH2Cl2/MeOH 9:1).

Workup

  1. customquenched with a saturated aqueous solution of NaHCO3 (75 mL)
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL)
  4. dry with materialdried over Na2SO4 the solvent
  5. customevaporated off under reduced pressure
  6. customThe crude residue was purified by silica gel column chromatography (CH2Cl2/MeOH 0.5-3.5%)

Sources & evidence

ORD record
ord-6e2e039254224937b41a27c7e01ebda0
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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