Ammonia → HCID 57508927, compound

HRID 2240830Notes

Reaction equation

HRID 2240830 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[C:22]4[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][C:23]=34)[O:16][N:15]=2)[CH:5]=[C:6]([CH3:13])[C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.[NH3:30]>>[NH2:30][CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:14]2[N:18]=[C:17]([C:19]3[S:20][CH:21]=[C:22]4[CH2:27][C:26]([CH3:28])([CH3:29])[CH2:25][CH2:24][C:23]=34)[O:16][N:15]=2)=[CH:5][C:6]=1[CH3:13]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 57508926HCID 57508926, compound

Product 1

HCID 57508927HCID 57508927, compound

Procedure

A solution of 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazole (500 mg, 1.18 mmol) in 2 N methanolic ammonia (7 mL) is heated in a sealed vial to 100° C. for 5 min in a microwave oven (300 W, active cooling during irradiation). The solvent is evaporated and the residue is purified by prep. HPLC (GROM-SIL ODS-4 HE, 75×30 mm ID, 10 μm, 20-95% acetonitrile in water containing 0.5% formic acid) to afford 1-amino-3-{4-[5-(5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (220 mg) as a colourless resin; LC-MS: tR=0.92 min, [M+1]+=428.38.

Workup

  1. temperature(300 W, active cooling during irradiation)
  2. customThe solvent is evaporated
  3. customthe residue is purified by prep

Sources & evidence

ORD record
ord-16ca393ab5f44260a3ecb36be357e950
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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