Hydrochloric Acid → HCID 178420789, compound

HRID 1273027Notes

Reaction equation

HRID 1273027 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[N:11](C2CCCCO2)[N:10]=[C:9]3[C:21]2[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=2)=[N:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[N:59]1[CH:64]=[CH:63][CH:62]=[C:61]([CH2:65][OH:66])[CH:60]=1.Cl>O1CCCC1>[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:14]=[C:13]([O:66][CH2:65][C:61]3[CH:60]=[N:59][CH:64]=[CH:63][CH:62]=3)[CH:12]=[C:8]([C:9]3[C:21]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:11][N:10]=3)[CH:7]=2)=[N:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178515986HCID 178515986, compound

Product 1

HCID 178420789HCID 178420789, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 3-(5-(1H-1,2,4-triazol-3-yl)-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)phenol (0.394 g, 0.65 mmol), triphenyl phosphine (0.685 g, 2.61 mmol), diethyl azodicarboxylate (0.41 mL, 2.61 mmol), 3-pyridylcarbinol (0.26 mL, 2.67 mmol) in tetrahydrofuran (2.5 mL) and was allowed to stir at room temperature overnight. To this mixture 6 N hydrogen chloride (20 mL) was added and allowed to stir at room temperature for 5 hours. This reaction was extracted with diethyl ether (3×), basified to pH˜11 with 6 N sodium hydroxide (aqueous), extracted with ethyl acetate (3×). The organic fractions were combined and dried with sodium sulfate, filtered, and condensed. The compound was purified by column chromatography (SiO2, 100% ethyl acetate in hexanes to 95% ethyl acetate in 5% methanol) and preparative HPLC (15–80% acetonitrile to H2O, 30 min.) (0.028 g, 12% yield over 2 steps): 1H NMR (CD3OD) δ 8.72 (m, 2H), 8.51 (dd, 1H), 8.11 (br s, 1H), 8.03 (dd, 1H), 7.68 (m, 3H), 7.50 (m, 2H), 7.13 (ddd, 1H), 5.30 (s, 2H); ES-MS (m/z) 369 [M+1]+.

Workup

  1. stirringto stir at room temperature for 5 hours
  2. extractionThis reaction was extracted with diethyl ether (3×)
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customcondensed
  7. customThe compound was purified by column chromatography (SiO2, 100% ethyl acetate in hexanes to 95% ethyl acetate in 5% methanol) and preparative HPLC (15–80% acetonitrile to H2O, 30 min.) (0.028 g, 12% yield over 2 steps)

Sources & evidence

ORD record
ord-6b340b972ae74b2dbc275ef5622466cc
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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