Hydrochloric Acid → HCID 178420715, compound

HRID 1353794Notes

Reaction equation

HRID 1353794 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C[C:25]([C:33]([OH:35])=O)([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)O)(C)(C)C.CCOC(/N=N/C(OCC)=O)=O.O1CCCCC1[N:54]1[C:62]2[C:57](=[CH:58][C:59]([C:63]3[N:67]=[CH:66][N:65](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:64]=3)=[CH:60][CH:61]=2)[C:56]([C:87]2[CH:88]=[C:89](O)[CH:90]=[CH:91][CH:92]=2)=[N:55]1.Cl>O1CCCC1>[NH:65]1[CH:66]=[N:67][C:63]([C:59]2[CH:58]=[C:57]3[C:62](=[CH:61][CH:60]=2)[NH:54][N:55]=[C:56]3[C:87]2[CH:88]=[CH:89][CH:90]=[C:91]([O:35][CH2:33][CH2:25][N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[CH:92]=2)=[N:64]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 224797613-(1-(Tetrahydro-2H-pyran-2-yl)-5-(1-trityl-1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)phenolHCID 69422963HCID 69422963, compound

Product 1

HCID 178420715HCID 178420715, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.694 g, 2.65 mmol), tetrahydrofuran (2.12 mL), tert-butylcarboxypiperazinylethanol (0.610 g, 2.65 mmol) and diethylazodicarboxylate (0.418 mL) were added to 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenol (0.400 g, 1.25 mmol). The mixture was stirred at ambient temperature for 21 h and poured into aqueous 6N hydrochloric acid (30 mL). After stirring at ambient temperature for 4 h, the mixture was extracted with ethyl acetate (3×). The aqueous fraction was added to aqueous 6N sodium hydroxide (30 mL) and the pH adjusted to 11. The solution was extracted with ethyl acetate (3×) and the organic fractions were combined and dried over anhydrous sodium sulfate, filtered and evaporated. The residue was stirred with trifluoracetic acid (3.0 mL) at ambient temperature for 70 min. Purification by preparative HPLC (5–70% acetonitrile/water) gave the title compound (0.132 g, 27% yield). ES-MS (m/z) 390 [M+1]+

Workup

  1. stirringAfter stirring at ambient temperature for 4 h
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. additionThe aqueous fraction was added to aqueous 6N sodium hydroxide (30 mL)
  4. extractionThe solution was extracted with ethyl acetate (3×)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue was stirred with trifluoracetic acid (3.0 mL) at ambient temperature for 70 min
  9. customPurification by preparative HPLC (5–70% acetonitrile/water)

Sources & evidence

ORD record
ord-dd175e4aa8b74d8e91e8939c4e61e073
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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