Dimethyl malonate → HCID 136348492, compound

HRID 510400Notes

Reaction equation

HRID 510400 reaction equation
[C:1]1([CH2:11][C:12]2[C:13]([NH2:18])=[N:14][NH:15][C:16]=2[NH2:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:19](OC)(=[O:25])[CH2:20][C:21](OC)=[O:22].C[O-].[Na+]>CO>[NH2:18][C:13]1[C:12]([CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[C:16]2[NH:17][C:19](=[O:25])[CH2:20][C:21](=[O:22])[N:15]2[N:14]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 712708004-(1-naphthalenylmethyl)-1H-pyrazole-3,5-diamine

Product 1

HCID 136348492HCID 136348492, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-(1-naphthalenylmethyl)-1H-pyrazole-3,5-diamine (2.18 g, 9.15 mmol), dimethyl propanedioate (3.63 g, 27.4 mmol) in Methanol (30 mL) was added sodium methoxide (1.68 g, 31.1 mmol). The reaction mixture was stirred at 65° C. for 18 h. After the reaction mixture was cooled down, the solvent was evaporated. Water (10 mL) was added in. The solid precipitated. The mixture was neutralized with 1 N HCl. The precipitated product was filtered and dried in vacuo (2.7 g, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.65 (s, 2H) 4.21 (s, 2H) 5.59 (br. s., 2H) 7.08 (d, J=6.82 Hz, 1H) 7.27-7.45 (m, 1H) 7.48-7.66 (m, 2H) 7.79 (d, J=8.34 Hz, 1H) 7.88-8.00 (m, 1H) 8.16 (d, J=8.34 Hz, 1H) 11.34 (s, 1H). LC/MS: MS (ES+) m/e 307.0 [M+H]+.

Workup

  1. temperatureAfter the reaction mixture was cooled down
  2. customthe solvent was evaporated
  3. additionWater (10 mL) was added in
  4. customThe solid precipitated
  5. filtrationThe precipitated product was filtered
  6. customdried in vacuo (2.7 g, 96%)

Sources & evidence

ORD record
ord-542b080ac552445dbea468c16ed3c12b
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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