1H-1,2,4-Triazole → HCID 59425454, compound

HRID 502260Notes

Reaction equation

[CH:1]([O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH:26]2[CH2:28][O:27]2)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].[Na].[NH:35]1[CH:39]=[N:38][CH:37]=[N:36]1>CN(C=O)C>[CH:1]([O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:29]3[CH2:30][CH2:31][CH2:32]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH:26]([OH:27])[CH2:28][N:35]2[CH:39]=[N:38][CH:37]=[N:36]2)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [4-(3-cyano-1-cyclobutyl-6-oxiranylmethoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (40 mg, 0.09 mmole) in DMF (1 mL) is added the sodium salt of 1,2,4-triazole (30 mg). The resulting mixture is stirred at 60° C. overnight. The solvent is removed under reduced pressure and the residue is diluted with ethyl acetate and then washed with water. The organic layer is concentrated and triturated with hexane. The precipitate is collected by filtration and washed well with 1/1 ethyl acetate/hexane and dried in vacuo to afford {4-[3-cyano-1-cyclobutyl-6-(2-hydroxy-3-[1,2,4]triazol-1-yl-propoxy)-1H-indol-2-yl]-phenyl}-carbamic acid isopropyl ester, compound 1420, (29 mg, 63%).

Workup

customThe solvent is removed under reduced pressure
additionthe residue is diluted with ethyl acetate
washwashed with water
concentrationThe organic layer is concentrated
customtriturated with hexane
filtrationThe precipitate is collected by filtration
washwashed well with 1/1 ethyl acetate/hexane
customdried in vacuo

Sources & evidence

ORD record: ord-d229ce0dca414fb1aae0fdfdc276a321
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772271B2

Reaction notes

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