Methyl iodide → HCID 59394981, compound

HRID 1465176Notes

Reaction equation

HRID 1465176 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:15]2)=[O:13])=[CH:7][C:6]=1[OH:29])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:32]I>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH3:32])[C:12]([CH:14]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:15]2)=[O:13])=[CH:7][C:6]=1[OH:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59395052HCID 59395052, compound

Product 1

HCID 59394981HCID 59394981, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-tert-butyl-3-hydroxyphenylcarbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate (50 mg, 0.13 mmol) in THF at 0° C. was added NaH (10 mg, 0.25 mmol) and the mixture stirred for 10 min. Methyl iodide (23 mg, 10 μL, 0.16 mmol) was added and mixture was stirred for 1 h at room temperature. HPLC purification (20-99% MeOH/water) provided ethyl 2-((4-tert-butyl-3-hydroxyphenyl) (methyl)carbamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate (18 mg, 32% yield). LC/MS m/z 413.0 [M+H]+. 1H NMR (400.0 MHz, DMSO-d6) δ 9.85 (s, 1H), 7.57 (d, J=6.9 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 7.00 (t, J=7.1 Hz, 1H), 6.88-6.79 (m, 4H), 4.79 (br s, 1H), 4.21-4.11 (m, 2H), 4.02-3.98 (m, 1H), 3.65 (d, J=13.4 Hz, 1H), 3.10 (s, 3H), 1.35 (s, 9H), 1.24 (t, J=7.1 Hz, 3H).

Workup

  1. stirringmixture was stirred for 1 h at room temperature
  2. customHPLC purification (20-99% MeOH/water)

Sources & evidence

ORD record
ord-688bd3005ca742cc8dd18ae09c63a774
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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