Hydrochloric Acid → HCID 117728195, compound

HRID 1772621Notes

Reaction equation

HRID 1772621 reaction equation
[N:1]1([C:7]2[C:8]3[N:9]([CH:23]=[C:24]([CH2:26][O:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[N:25]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([O:21]C)=[O:20])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.O>[N:1]1([C:7]2[C:8]3[N:9]([CH:23]=[C:24]([CH2:26][O:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[N:25]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117727959HCID 117727959, compound

Product 1

HCID 117728195HCID 117728195, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 15b (500 mg, 0.960 mmol) in THF (20 mL) was added a solution of LiOH (100 mg, 4.18 mmol) in H2O (5 mL). The resulting solution was stirred at rt overnight, and then diluted with H2O (20 mL). The pH of the solution was adjusted to 3 with 2 N HCl solution. The resulting solids were collected by filtration and washed with Et2O to obtain compound 15c as a yellow solid (350 mg, 72% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H23N9O2: 482.2 (M+H). Found 482.0.

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. washwashed with Et2O

Sources & evidence

ORD record
ord-918dd6b4b3a04182923e1f961a313dcf
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…