Isopropanol → HCID 58044026, compound

HRID 1918821Notes

Reaction equation

HRID 1918821 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[CH:12][N:11]=2)=[CH:5][C:4]([C:23]2[CH:33]=[CH:32][CH:31]=[C:30]([N:34]3[CH2:46][CH2:45][N:37]4[C:38]5[CH2:39][CH2:40][CH2:41][CH2:42][C:43]=5[CH:44]=[C:36]4[C:35]3=[O:47])[C:24]=2[CH2:25][O:26]C(=O)C)=[CH:3]1.O[Li].O.C1COCC1.C(O)(C)C>O>[OH:26][CH2:25][C:24]1[C:23]([C:4]2[CH:5]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[CH:12][N:11]=3)[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=2)=[CH:33][CH:32]=[CH:31][C:30]=1[N:34]1[CH2:46][CH2:45][N:37]2[C:38]3[CH2:39][CH2:40][CH2:41][CH2:42][C:43]=3[CH:44]=[C:36]2[C:35]1=[O:47]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67016356HCID 67016356, compound

Product 1

HCID 58044026HCID 58044026, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-mL, single-necked, round-bottomed flask equipped with a magnetic stirring bar was charged with 113b (105 mg, 0.17 mmol), LiOH.H2O (35 mg, 0.83 mmol), THF (2 mL), isopropanol (2 mL), and water (1 mL). After the reaction mixture was stirred at room temperature for 3 h, it was partitioned between dichloromethane (5 mL) and water (5 mL), and the organic phase was extracted with dichloromethane (5 mL×3). The combined organic phases were washed with water (5 mL×2) and brine (5 mL×1), dried (Na2SO4), and concentrated. The crude product was re-dissolved in dichloromethane (3 mL). To this solution was added hexane (10 mL) and the resulting precipitates were filtered to give 80% yield (79 mg) of 2-(2-hydroxymethyl-3-{1-methyl-5-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-3,4,6,7,8,9-hexahydro-2H-pyrazino[1,2-a]indol-1-one 113; MS (ESI+) m/z 594.3 (M+H).

Workup

  1. customA 100-mL, single-necked, round-bottomed flask equipped with a magnetic stirring bar
  2. customit was partitioned between dichloromethane (5 mL) and water (5 mL)
  3. extractionthe organic phase was extracted with dichloromethane (5 mL×3)
  4. washThe combined organic phases were washed with water (5 mL×2) and brine (5 mL×1)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe crude product was re-dissolved in dichloromethane (3 mL)
  8. additionTo this solution was added hexane (10 mL)
  9. customthe resulting precipitates
  10. filtrationwere filtered

Sources & evidence

ORD record
ord-89aeb88dbdc841aab067e31c393a7910
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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