Isopropanol → 2-(3-(6-(1-cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)-phenyl)-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-1(2H)-one

HRID 1918824Notes

Reaction equation

HRID 1918824 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([N:12]2[CH2:24][CH2:23][N:15]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=4[CH:22]=[C:14]3[C:13]2=[O:25])=[CH:10][CH:9]=[CH:8][C:7]=1[C:26]1[N:27]=[C:28]([NH:34][C:35]2[CH:36]=[N:37][N:38]([CH:40]3[CH2:42][CH2:41]3)[CH:39]=2)[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=1)(=O)C.C1COCC1.CC(O)C.O[Li].O>O>[CH:40]1([N:38]2[CH:39]=[C:35]([NH:34][C:28]3[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=[C:26]([C:7]4[C:6]([CH2:5][OH:4])=[C:11]([N:12]5[CH2:24][CH2:23][N:15]6[C:16]7[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=7[CH:22]=[C:14]6[C:13]5=[O:25])[CH:10]=[CH:9][CH:8]=4)[N:27]=3)[CH:36]=[N:37]2)[CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 670161882-(6-(1-Cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-6-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)benzyl Acetate

Product 1

HCID 580443052-(3-(6-(1-cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)-phenyl)-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-1(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round-bottomed flask equipped with a stirring bar, 114c THF (1.25 mL), i-PrOH (1.25 mL), H2O (1.25 mL), LiOH H2O (135 mg) were added. The resulting mixture was stirred at RT for 1 hr. Removed all the solvent in vacuo and silica gel column chromatography (MeOH:DCM=10:90) gave 38.6 mg 2-(3-(6-(1-cyclopropyl-1H-pyrazol-4-ylamino)-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-(hydroxymethyl)-phenyl)-3,4,6,7,8,9-hexahydro-pyrazino[1,2-a]indol-1(2H)-one 114 as a yellow solid. MS (ESI+) m/z 526.3 (M+H).

Workup

  1. customTo a round-bottomed flask equipped with a stirring bar
  2. customRemoved all the solvent in vacuo and silica gel column chromatography (MeOH:DCM=10:90)

Sources & evidence

ORD record
ord-b1872428ffb745e9befbf00ea9716c2a
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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