Sodium Hydroxide → HCID 9944712, compound

HRID 1744444Notes

Reaction equation

HRID 1744444 reaction equation
[C:1]([C:3]1[C:4](=N)[O:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)=[CH:10][CH:9]=[C:8]1[N:20]([CH3:23])[CH:21]=[CH:22][C:7]=21)#[N:2].[OH-:25].[Na+]>Cl.CS(C)=O.O>[C:1]([C:3]1[C:4](=[O:25])[O:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1)=[CH:10][CH:9]=[C:8]1[N:20]([CH3:23])[CH:21]=[CH:22][C:7]=21)#[N:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22229226HCID 22229226, compound

Product 1

HCID 9944712HCID 9944712, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 3-cyano-2-imino-4-(5-methyl-pyridin-3-yl)-7-methyl-2H-pyrrolo[2,3-h]chromene (50 mg, 0.14 mmol) in 10% HCl (2 mL) and DMSO (0.5 mL) was stirred at room temperature for approximately 4 h. The yellow suspension was diluted with water (5 mL), neutralized to approximate pH=9 using 10% NaOH, and extracted with EtOAc (3×20 mL). The EtOAc extracts were washed with brine (10 mL), dried over MgSO4, and evaporated to yield a yellow solid. The solid was purified by flash column chromatography (silica gel, EtOAc:hexanes, 50-80% EtOAc) to yield a yellow solid (31 mg, 68%). 1H NMR (DMSO-d6): 8.71 (d, J=1.8 Hz, 1H), 8.58 (d, J=2.1 Hz, 1H), 7.88 (m, 1H), 7.61 (d, J=3.0 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H) 6.93 (d, J=8.7 Hz, 1H), 6.91 (d, J=3.3 Hz, 1H), 3.88 (s, 3H), 2.45 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe EtOAc extracts were washed with brine (10 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto yield a yellow solid
  6. customThe solid was purified by flash column chromatography (silica gel, EtOAc:hexanes, 50-80% EtOAc)

Sources & evidence

ORD record
ord-0f3cd171c13345798b4a6131072952cb
Source dataset
uspto-grants-2006_03
Patent number
US07015328B2

Reaction notes

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