Tetrahydrofuran → HCID 58173259, compound

HRID 2047012Notes

Reaction equation

HRID 2047012 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][NH:25][CH:24]([C:27]([O:29]C)=[O:28])[CH2:23][CH2:22]2)[C:3]=1[Br:31].C1COCC1.[OH-].[Na+]>O>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([CH:21]2[CH2:26][NH:25][CH:24]([C:27]([OH:29])=[O:28])[CH2:23][CH2:22]2)[C:3]=1[Br:31]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58173435HCID 58173435, compound

Product 1

HCID 58173259HCID 58173259, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-2-carboxylate (11 mg, 0.023 mmol) in 2:1 THF:H2O (1.5 mL) was treated with 2N NaOH(aq) (0.25 mL). The resulting solution was stirred at room temperature for 18 hours. This solution is reduced in vacuo and purified by prep-LC to afford the title compound (8.9 mg): LC/MS RT=2.16 min. Mass calculated for, M+H 467.08, observed 467.08.

Workup

  1. custompurified by prep-LC

Sources & evidence

ORD record
ord-9204f0d92fc34e238f1637b9baa89043
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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