Hydrochloric Acid → HCID 58173412, compound

HRID 2047013Notes

Reaction equation

HRID 2047013 reaction equation
C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[C:16]([Br:17])=[C:15]([NH2:18])[N:14]3[N:19]=[CH:20][C:21]([C:22]4[CH:23]=[N:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[CH:27][CH:26]=5)=[C:13]3[N:12]=2)[CH2:7][NH:6]1)=[O:4].[CH3:32][O:33][CH2:34][C:35](Cl)=[O:36].C(N(CC)CC)C.[OH-].[Na+].Cl>C1COCC1.CN(C=O)C>[NH2:18][C:15]1[N:14]2[N:19]=[CH:20][C:21]([C:22]3[CH:23]=[N:24][C:25]4[C:30]([CH:31]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:13]2[N:12]=[C:11]([CH:8]2[CH2:7][N:6]([C:35](=[O:36])[CH2:34][O:33][CH3:32])[CH:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)[C:16]=1[Br:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chlorideHCID 58173435HCID 58173435, compound

Product 1

HCID 58173412HCID 58173412, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(7-amino-6-bromo-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-piperidine-2-carboxylic acid methyl ester (20 mg, 0.042 mmol), methoxy-acetyl chloride (13 mg, 0.071 mmol) and triethylamine (0.024 ml, 0.167 mmol) in THF:DMF (0.5 ml:0.5 ml) was stirred at room temperature for 16 h. The crude mixture was treated with 2.0 N sodium hydroxide solution (0.14 ml) at room temperature for 16 h. The reaction mixture was acidified with 1.0 N aqueous hydrogen chloride solution (0.5 ml), concentrated and purified by prep-LC to afford the title compound (7.94 mg): LC/MS RT=3.06 min. Mass calculated for, M+H 539.10, observed 539.10.

Workup

  1. concentrationconcentrated
  2. custompurified by prep-LC

Sources & evidence

ORD record
ord-c468b83755724c29969cff17fdc86ca0
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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