Methyl iodide → HCID 86602762, compound

HRID 349719Notes

Reaction equation

[C:1](=O)([O-])[O-].[K+].[K+].CI.[F:9][C:10]([F:42])([F:41])[C:11]1[CH:12]=[C:13]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:14][O:15][CH2:16][C:17]([OH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][CH2:19][NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23]>CC(C)=O>[F:9][C:10]([F:41])([F:42])[C:11]1[CH:12]=[C:13]([CH:34]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:36]=1)[CH2:14][O:15][CH2:16][C:17]([OH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][CH2:19][N:20]([CH3:1])[C:21](=[O:26])[C:22]([F:24])([F:25])[F:23]

Participants

Conditions

Temperature: 60 °C

Procedure

Excess amount of potassium carbonate (150 mg, 1.1 mmol) and excess amount of methyl iodide (0.040 ml, 0.064 mmol) were mixed with N-(4-(3,5-bis(trifluoromethyl)benzyloxy)-3-hydroxy-3-phenylbutyl)-2,2,2-trifluoroacetamide (15 mg, 0.030 mmol) in acetone (2 ml). The reaction mixture was heated in microwave at 60° C. for 10 minutes. The salt precipitate was filtered off and the filtrate was concentrated. The residue was purified by preparative HPLC to give the desired N-methylacetamide. 1H NMR (300 MHz, MeOH) δ ppm 7.84 (s, 3 H) 7.46–7.54 (m, 2 H) 7.35 (ddd, J=8.14, 6.50, 4.76 Hz, 2 H) 7.22–7.30 (m, 1 H) 4.61–4.73 (m, 2 H) 3.62–3.75 (m, 2 H) 3.40–3.55 (m, 1 H) 3.11–3.37 (m, 1 H) 3.01 (s, 2 H) 2.93 (s, 1 H) 2.15–2.31 (m, 2 H); LRMS [ESI, (MH+−H2O)] m/z calcd for C22H19NO2F9 500.13, found 499.97.

Workup

filtrationThe salt precipitate was filtered off
concentrationthe filtrate was concentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-236a32c39eb341eb8402398e1e421f83
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179926B2

Reaction notes

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