Methyl iodide → HCID 16005230, compound

HRID 1175601Notes

Reaction equation

[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:24])([CH3:23])[C:16]([NH:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])=[CH:11][CH:10]=2)[CH:6]=[N:5][CH:4]=1.[OH-].[K+].[CH3:27]I>CS(C)=O>[CH2:19]([NH:18][C:16](=[O:17])[C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:7]2[CH:6]=[N:5][CH:4]=[C:3]([CH2:2][O:1][CH3:27])[N:8]=2)=[CH:14][CH:13]=1)([CH3:23])[CH3:24])[CH:20]([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(4-(6-(Hydroxymethyl)pyrazin-2-yl)phenyl)-N-isobutyl-2-methylpropanamide (example 29a) (37 mg, 0113 mmol) in DMSO (1 mL) was added under argon to a solution of KOH (9.5 mg, 0.169 mmol) in DMSO (1 mL) and the mixture was stirred for 5 min then cooled to 0° C. MeI (7.7 μL, 0.124 mmol) in DMSO (1 mL) was added dropwise and the mixture was stirred at room temperature for 20 min. The reaction was quenched with water (100 μL) and the product was purified by RP HPLC (water-acetonitrile) to give 19 mg (50%) of the product. 1H NMR (400 MHz, dMSO): δ 0.73-0.75 (d, 6H), 1.49 (s, 6H), 1.68-1.71 (m, 1H), 2.83-2.86 (m, 2H), 3.37 (s, 3H), 4.63 (s, 2H), 7.37 (t, 1H), 7.45-7.48 (d, 2H), 8.07-8.09 (d, 2H), 8.60 (s, 1H), 9.16 (s, 1H); MS+H (342).

Workup

stirringthe mixture was stirred at room temperature for 20 min
customThe reaction was quenched with water (100 μL)
customthe product was purified by RP HPLC (water-acetonitrile)

Sources & evidence

ORD record: ord-0710463ae5534a12a3e829da48a8d1d6
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842324B2

Reaction notes

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