Methanol → HCID 66747529, compound

HRID 2401899Notes

Reaction equation

HRID 2401899 reaction equation
[C:1]([C:3]1[C:4]([CH2:18][N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20]2)=[C:5]([C:14]([O:16]C)=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].O.CO.[OH-].[Na+:34]>O1CCCC1.O.CO>[Na+:34].[C:1]([C:3]1[C:4]([CH2:18][N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20]2)=[C:5]([C:14]([O-:16])=[O:15])[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 14798Sodium HydroxideHCID 66748126HCID 66748126, compound

Product 1

HCID 66747529HCID 66747529, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 4-cyano-5-(morpholin-4-yl)-3-[(4-oxoquinazolin-3(4H)-yl)methyl]thiophene-2-carboxylate (0.139 g, 0.339 mmol) was dissolved in Tetrahydrofuran (15.0 mL), Water (2.0 mL) and Methanol (5.0 mL). 1.00 M of Sodium hydroxide in Water (1.0 mL, 1.0 mmol) was added and the homogeneous solution was stirred at room temperature for 24 hours. The solution was concentrated in rotavapor to give a white crude solid, dissolved in H2O/MeOH (1/10, ˜20 mL) and concentrated in rotavapor until a white suspension (˜2 mL volume). The suspension was filtered to collect the solid, dried in lypholizer to give a white solid product (0.132 g, yield 92.2%). LC/MS: (FA) ES+ 397; ES− 395. 1H NMR (400 MHz, d4-methanol) δ 8.37 (s, 1H), 8.22 (d, J=8.03 Hz, 1H), 7.78-7.82 (m, 1H), 7.65 (d, J=7.28 Hz, 1H), 7.51-7.55 (m, 1H), 5.99 (s, 2H), 3.78-3.81 (m, 4H), 3.47-3.50 (m, 4H).

Workup

  1. concentrationThe solution was concentrated in rotavapor
  2. customto give a white crude solid
  3. concentrationconcentrated in rotavapor until a white suspension (˜2 mL volume)
  4. filtrationThe suspension was filtered
  5. customto collect the solid
  6. customdried in lypholizer

Sources & evidence

ORD record
ord-9ffbc306574c4312a9e568c5f393a8af
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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