Methyl iodide → HCID 68182710, compound

HRID 1623945Notes

Reaction equation

HRID 1623945 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([C:12]1[C:13]2[CH2:14][C@H:15]3[CH2:28][C@H:16]3[C:17]=2[N:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[N:19]=1)=[O:11].I[CH3:30]>CN(C=O)C>[CH3:30][N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[C:10]([C:12]1[C:13]2[CH2:14][C@H:15]3[CH2:28][C@H:16]3[C:17]=2[N:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[N:19]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68182611HCID 68182611, compound

Product 1

HCID 68182710HCID 68182710, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a reaction vial containing NaH (2.3 mg, 0.057 mmol) was added (1aR,5aR)-2-(2,4-difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid pyridin-2-ylamide (10 mg, 0.028 mmol) in DMF (0.5 mL) under nitrogen protection. After 15 min, iodomethane (2.7 μL, 0.043 mmol) in DMF (0.1 mL) was added. The reaction mixture was stirred at room temperature overnight, and then purified by preparative LCMS to give the title compound (3.5 mg). LCMS m/z=367.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.52 (td, J=4.7 and 3.4 Hz, 1H), 1.15-1.22 (m, 1H), 2.19-2.23 (m, 1H), 2.28-2.34 (m, 1H), 2.97 (dd, J=16.6 Hz, 1H), 3.08 (dd, J=16.4 and 6.3 Hz, 1H), 4.39 (s, 3H), 6.97-7.08 (m, 2H), 7.49 (t, J=6.6 Hz, 1H), 7.88-7.94 (m, 1H), 8.22 (t, J=8.0 Hz, 1H), 8.50-8.55 (m, 2H).

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-a11846e574444348b6a6cc0e1f2831ad
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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