Methyl iodide → HCID 11567441, compound

HRID 732151Notes

Reaction equation

[CH:1](NC(C)C)(C)C.[Li]CCCC.[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([C@H:25]([O:27][C:28]3[N:29]([CH3:39])[C:30]([C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)=[N:31][N:32]=3)[CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1.CI.[NH4+].[Cl-]>C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([C:20]2[O:24][N:23]=[C:22]([C:25]([CH3:1])([O:27][C:28]3[N:29]([CH3:39])[C:30]([C:33]4[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=4)=[N:31][N:32]=3)[CH3:26])[N:21]=2)[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of diisopropylamine (55.0 ml, 0.39 mmol) in THF (3 ml) at 0° C. was added nBuLi (2.5M, hex., 135 ml) slowly. After 20 minutes the mixture was cooled to −78° C. and (−)-4-(5-{(1R)-1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethoxy}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine (107 mg, 0.28 mmol) in THF (2 ml) was added. The resulting mixture was stirred for 45 minutes before CH3I (22 ml, 0.34 mmol) was added and the reaction mixture was stirred for 1 h at r.t. Sat. NH4Cl solution was added and the mixture was extracted with EA. The organic phase was washed with H2O and brine, dried and evaporated. Purification of the residue by silica gel chromatography using CHCl3:MeOH 50:1 followed by prep. HPLC gave the title compound (22 mg, 20%). 1H-NMR: 2.11 (s, 6 H) 3.63 (s, 3 H) 7.45 (d, 1 H) 7.52-7.57 (m, 1 H) 7.59 (d, 2 H) 7.98 (d, 1 H) 8.09 (s, 1 H) 8.72 (d, 2 H)

Workup

additionwas added
extractionthe mixture was extracted with EA
washThe organic phase was washed with H2O and brine
customdried
customevaporated
customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record: ord-56f2a869ecf2409eb5120e7192556206
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585881B2

Reaction notes

Loading…