Trifluoroacetic acid → HCID 22235374, compound

HRID 1743716Notes

Reaction equation

HRID 1743716 reaction equation
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([NH:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:17][CH:16]3[N:18](C(OC(C)(C)C)=[O:20])[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH4+:2].[OH-:20].[CH:16]12[NH:18][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:27][CH:26]=1)[CH2:17]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22235550HCID 22235550, compound

Product 2

HCID 14923Ammonium HydroxideHCID 22235374HCID 22235374, compoundYield 739.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-[3-(4-cyanoanilino)propyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (4.7 g, 2.7 mmol; from step (a) above) in CH2Cl2 (600 mL) was added TFA (90 mL). The resulting solution was stirred for 1 h and concentrated in vacuo. Flash chromatography on silica gel eluting with CH2Cl2:MeOH:concentrated NH4OH (94:5:1) gave 2.7 g (79%) of the title compound as an oil.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7c886d5cef041a18806ed8bd8682500
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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