Hydrochloric Acid → HCID 178519329, compound

HRID 1947011Notes

Reaction equation

HRID 1947011 reaction equation
C([BH-](CC)CC)C.[Li+].C[O:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[N:18][N:19]2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]3)[N:23]=2)=[CH:15][CH:14]=1)=O.Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.CC(O)=O.CCO>[OH:10][CH2:11][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[N:18][N:19]2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]3)[N:23]=2)=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23664628LithiumtriethylborohydrideHCID 178497300HCID 178497300, compound

Product 1

HCID 178519329HCID 178519329, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of lithium triethylborohydride (1 M in THF, 0.8 mL) was slowly added at RT to trans-1-[2-(4-hydroxycyclohexylamino)-pyrimidin-4-yl]-1H-indazole-6-carboxylic acid methyl ester (100 mg) in THF (3 mL). The resulting mixture was stirred for 30 min, and AcOH/EtOH (1:1, 2 mL) was added. The reaction mixture was stirred for 30 min, then poured onto aqueous HCl (0.1 M). The resulting mixture was basified to pH 8 with aqueous NaOH and aqueous NaHCO3, then extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH, 95:5) to give of trans-4-[4-(6-hydroxymethyl-indazol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (22 mg) as a white solid. MS=340 [M+H]+; MP=216.0-217.7° C.

Workup

  1. stirringThe reaction mixture was stirred for 30 min
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by preparative TLC (DCM/MeOH, 95:5)

Sources & evidence

ORD record
ord-e00e811e9fe5487a833b8df376157721
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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