HCID 178481571, compound → HCID 178481569, compound

HRID 1490105Notes

Reaction equation

HRID 1490105 reaction equation
[CH2:1]1[CH2:6][CH:5]([C:7]2([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26](NC4NN=NN=4)[CH:25]=3)=[O:22])[N:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]([CH3:18])[C:8]2=[O:19])[CH2:4][CH2:3][CH2:2]1.[NH:36]1[C:40]([NH:41][CH2:42]C2C=C(C=CC=2)N)=[N:39][N:38]=[N:37]1>C(#N)C>[CH2:3]1[CH2:4][CH:5]([C@@:7]2([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH2:42][NH:41][C:40]4[NH:39][N:38]=[N:37][N:36]=4)[CH:25]=3)=[O:22])[N:13]=[CH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]([CH3:18])[C:8]2=[O:19])[CH2:6][CH2:1][CH2:2]1

Participants

4

Reactant 2

HCID 178481571HCID 178481571, compoundHCID 178507567HCID 178507567, compound

Product 1

HCID 178481569HCID 178481569, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from Intermediate 3 and 3-[(tetrazol-5-yl)aminomethyl]aniline using a similar method to that described for Example 4, except that anhydrous acetonitrile was used instead of tetrahydrofuran; the crude product was purified by flash chromatography (silica gel, dichloromethane-methanol, 95:5 to 90:10) and recrystallized from a mixture of methanol and ethyl acetate; mp 175°-178° C.; [α]D24 +17.4° (c=0.50, dimethylformamide); the spectroscopic properties of this material (1 H-NMR and MS spectra) were identical to those described for its racemate (Example 1).

Workup

  1. customthe crude product was purified by flash chromatography (silica gel, dichloromethane-methanol, 95:5 to 90:10)
  2. customrecrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-faad67cb2b5b4f99918d43941d43b365
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

Loading…