Sodium Hydroxide → (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

HRID 1362219Notes

Reaction equation

HRID 1362219 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+]>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]([OH:34])=[O:3])[CH2:11][C:10]=2[CH:12]=1)=[O:32]

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 9980301(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 acidYield 48%

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 (0.40 g, 0.87 mmol) in methanol (30 mL) was treated with 1N NaOH (10 mL, 10 mmol). The mixture was heated at reflux for 2 h. After cooling, the methanol was evaporated. The residue was diluted with H2O (15 mL) and neutralized to pH 6 with 2N HCl. The solid was collected by filtration, and triturated subsequently with a mixture CH3CN/H2O (9:1, v/v), diethyl ether, and methanol to give the title compound (180 mg, 48%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 12.78 (s, 1H), 10.09-10.06 (m, 1H), 8.39-8.36 (m, 1H), 8.01-7.92 (m, 1H), 7.57-7.39 (m, 3H), 7.26-6.69 (m, 3H), 6.42-6.18 (m, 1H), 5.04-4.85 (m, 2H), 4.53-4.48 (m, 2H), 4.05-4.01 (m, 2H), 3.72-3.68 (m, 3H), 3.11-2.99 (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. customthe methanol was evaporated
  5. additionThe residue was diluted with H2O (15 mL)
  6. filtrationThe solid was collected by filtration
  7. customtriturated subsequently with a mixture CH3CN/H2O (9:1

Sources & evidence

ORD record
ord-b9e8468ec10646a0984c6e369af2bd6b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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