1-Chloro-N,N-2-trimethylpropenylamine → 4-(4-chlorophenyl)-1-cyclopropyl-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one

HRID 873827Notes

Reaction equation

HRID 873827 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:9]2[C:10]([CH3:20])=[N:11][N:12]([CH:17]3[CH2:19][CH2:18]3)[C:13]=2[C:14](O)=[O:15])=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:10]([CH3:20])=[N:11][N:12]([CH:17]4[CH2:18][CH2:19]4)[C:13]=3[C:14](=[O:15])[N:21]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 1177028014-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 1177026894-(4-chlorophenyl)-1-cyclopropyl-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-oneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-((4-chlorophenyl)((4-methoxybenzyl)amino)methyl)-1-cyclopropyl-3-methyl-1H-pyrazole-5-carboxylic acid (Step 23.7) (2.30 g, 4.59 mmol) in CH2Cl2 (30 mL) under Ar was added 1-chloro-N,N,2-trimethyl-1-propenylamine (0.846 mL, 6.43 mmol) at 0° C. The reaction mixture was stirred for 1 hr at rt, quenched with a saturated aqueous solution of NaHCO3 (75 mL), and extracted with CH2Cl2 (2×100 mL) The combined organic layers were washed with a saturated aqueous solution of NaHCO3 (100 mL), dried (Na2SO4) and evaporated. The crude material was purified by silica gel column chromatography (Hex/EtOAc 5-30%) to afford the title product (1.82 g, 4.24 mmol, 92% yield) as a yellow oil. tR: 5.76 min (HPLC 1); tR: 1.27 min (LC-MS 2); ESI-MS: 408 [M+H]+ (LC-MS 2); Rf=0.66 (hexane/EtOAc 1:1).

Workup

  1. customquenched with a saturated aqueous solution of NaHCO3 (75 mL)
  2. extractionextracted with CH2Cl2 (2×100 mL) The combined organic layers
  3. washwere washed with a saturated aqueous solution of NaHCO3 (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude material was purified by silica gel column chromatography (Hex/EtOAc 5-30%)

Sources & evidence

ORD record
ord-cc1adde9380a4e8083a4e6c0ea58c370
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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