Trifluoroacetic acid → Ammonia

HRID 2353199Notes

Reaction equation

HRID 2353199 reaction equation
[C:1]([O:5]C([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:16]=[N:17][C:18]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:20]=1)=O)(C)(C)[CH3:2].F[C:30](F)(F)[C:31]([OH:33])=[O:32].[OH-:36].[Na+]>ClCCl>[NH3:8].[C:31]([OH:33])(=[O:32])/[CH:30]=[CH:2]/[C:1]([OH:5])=[O:36].[C:23]1([C:22]#[C:21][C:18]2[N:17]=[N:16][C:15]([N:11]3[CH2:10][C@@H:9]4[CH2:14][C@H:12]3[CH2:13][NH:8]4)=[CH:20][CH:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68444255HCID 68444255, compound

Product 2

HCID 222AmmoniaHCID 131728240HCID 131728240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[6-phenylethynyl-pyridazin-3-yl]-(1S,4S)-2,5-diaza-bicyclo-[2.2.1]heptane-2-carboxylic acid tert-butyl ester (1.95 g; 5.2 mmol), trifluoroacetic acid (8.0 ml; 104 mmol) and dichloromethane (20 ml) was stirred for 2 hours at room temperature. Aqueous sodium hydroxide (20 ml; 4 M) was added. The mixture was extracted with dichloromethane (3×20 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.85 g (59%). The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp. 173.1-174.4° C.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×20 ml)

Sources & evidence

ORD record
ord-e5bd0f72037546bda91f59691f2d222e
Source dataset
uspto-grants-2010_07
Patent number
US07750011B2

Reaction notes

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