Lithium hydroxide, monohydrate → HCID 58299639, compound

HRID 79208Notes

Reaction equation

HRID 79208 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:25][CH2:24]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][N:37]=[CH:38][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].C(#N)C.O>CO.O>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([CH2:22][N:23]5[CH2:24][CH2:25][N:26]([CH2:29][C:30]([OH:32])=[O:31])[CH2:27][CH2:28]5)=[CH:18][CH:17]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:35]=[CH:36][N:37]=[CH:38][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 18373917Acetonitrile--water (1/1)HCID 58299758Ethyl (4-((6-((9-cyclopentyl-9 H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)methyl)-1-piperazinyl)acetate

Product 1

HCID 58299639HCID 58299639, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of compound 347 (50 mg, 97 μmol) and lithium hydroxide, monohydrate (14 μl, 486 μmol) in methanol (9 mL) and water (3 mL) was heated at reflux for 2 h. After cooling, the crude mixture was subjected to reverse phase preparative HPLC (acetonitrile/H2O containing 0.1% TFA each, 40 min from 10 to 40%). Lyophilization provided compound 349 (40 mg) as a light yellow solid (TFA salt). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.84 (1 H, s), 9.62 (1 H, s), 9.38 (1 H, s), 8.68 (1 H, d, J=5.9 Hz), 8.58 (1 H, d, J=6.3 Hz), 8.26-8.48 (2 H, m), 7.89-8.01 (1 H, m), 5.40 (1 H, quin, J=8.9 Hz), 2.75-4.63 (12 H, m), 2.39-2.47 (2 H, m), 2.01-2.23 (4 H, m), 1.70-1.87 (2 H, m). LCMS-ESI (POS), M/Z, M+1: Found 487.3.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. custom40 min

Sources & evidence

ORD record
ord-bf2f0970c7c041a999dea9a429390649
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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