Sodium Hydroxide → Sodium (E)-(6-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetate

HRID 1711908Notes

Reaction equation

HRID 1711908 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]1[CH2:11][C:10]2[CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18](=[O:32])[N:19]([CH3:31])[CH2:20][C:21]3[N:22]([CH3:30])[C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:14]=[N:15][C:9]=2[NH:8][C:7]1=[O:33])C.[OH-].[Na+:36]>CO>[CH3:31][N:19]([CH2:20][C:21]1[N:22]([CH3:30])[C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18](/[CH:17]=[CH:16]/[C:13]1[CH:14]=[N:15][C:9]2[NH:8][C:7](=[O:33])[N:6]([CH2:5][C:4]([O-:34])=[O:3])[CH2:11][C:10]=2[CH:12]=1)=[O:32].[Na+:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66967165(E)-(6-{2-[Methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester

Product 1

HCID 66967355Sodium (E)-(6-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (E)-(6-{2-[methyl-(1-methyl-1H-indol-2-ylmethyl)carbamoyl]vinyl}-2-oxo-1,4-dihydro-2H-pyrido[2,3-d]pyrimidin-3-yl)acetic acid ethyl ester (0.19 g, 0.40 mmol) in methanol (20 mL) was treated with 1N NaOH (0.80 mL, 0.80 mmol). The mixture was heated at reflux for 2 h. After cooling, the solid was collected by filtration to give the title compound (140 mg, 77%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6+D2O) δ 8.30-8.25 (m, 1H), 7.97-7.86 (m, 1H), 7.55-7.42 (m, 3H), 7.17-7.05 (m, 3H), 6.46-6.22 (m, 1H), 5.03-4.86 (m, 2H), 4.55 (s, 1H), 4.48 (s, 1H), 3.76-3.67 (m, 5H), 3.13-3.05 (m, 3H); MS (ESI) m/e 434 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-633d3a1cf06a4ca0b01978ddd182ac88
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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