Trifluoroacetic acid → HCID 178518658, compound

HRID 1363211Notes

Reaction equation

HRID 1363211 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:29])[N:16]4[C@H:19]4[CH2:24][CH2:23][C@H:22]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:20]4)=[CH:12][N:11]=3)[C:6]=2[CH:30]=1.[OH-].[K+].C(O)(C(F)(F)F)=O>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:29])[N:16]4[C@H:19]4[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]4)=[CH:12][N:11]=3)[C:6]=2[CH:30]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 178501189HCID 178501189, compound

Product 1

HCID 178518658HCID 178518658, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of trans-methyl 4-(2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-7,8-dihydropurin-9-yl)cyclohexanecarboxylate (5 mg) in THF was treated with an aqueous solution of KOH (35 mg) in 2 mL of water. The mixture was heated at 50° C. for 12 hours. The mixture was acidified with TFA and concentrated. Silica gel chromatography (60:30:10 DCM:EtOAc:MeOH) provided 4.3 mg of the title compound. 1H-NMR (300 MHz, CDCl3) δ 9.0 (s, 1H), 8.3 (dd, 1H), 8.1 (s, 1H), 7.7 (dd, 1H), 7.1 (td, 1H), 4.3 (m, 1H), 2.4 (m, 3H), 2.2 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f7ad31053b154430982cdc0af5dd3b37
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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