Hydrochloric Acid → HCID 24822774, compound

HRID 1925338Notes

Reaction equation

HRID 1925338 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=[CH:11]2.[CH:21]1[C:25]2[C:26](Cl)=[N:27][CH:28]=[N:29][C:24]=2[NH:23][CH:22]=1.Cl>CS(C)=O>[N:29]1[C:24]2[NH:23][CH:22]=[CH:21][C:25]=2[C:26]([O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=[CH:11]3)=[N:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 24822774HCID 24822774, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (23.4 g, 71.9 mmol) was added in one portion to a solution of 6-hydroxy-1-naphthoic acid (5.41 g, 28.7 mmol) and 6-chloro-7-deazapurine (3.68 g, 24.0 mmol) in DMSO (47.9 ml) at RT. The resulting mixture was heated to 100° C. and stirred for 14 hours. The mixture was cooled to RT and neutralized to a pH of 7 with 6N HCl. Solid material proceeded to crash out of solution. The entire mixture was centrifuged and the liquid was decanted. To the solid was added saturated aqueous NaHCO3 and the resulting mixture was agitated over night on a rotating plate. The mixture was centrifuged again and decanted into a 1 L flask. The solution was acidified to neutral pH, centrifuged again and decanted. EtOAc was added to the solid material, the mixture centrifuged and the liquid was decanted to reveal the desired compound. MS (ESI, pos. ion) m/z: 306.1 (M+1). Mass Calc'd for C18H15NO3: 305.08.

Workup

  1. customthe liquid was decanted
  2. additionTo the solid was added saturated aqueous NaHCO3
  3. stirringthe resulting mixture was agitated over night on a rotating plate
  4. customdecanted into a 1 L flask
  5. customdecanted
  6. additionEtOAc was added to the solid material
  7. customthe liquid was decanted

Sources & evidence

ORD record
ord-a8649a11d2fc4a078fa72e98acd5d35b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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