Methanol → (3-Ethynyl-pyrrolidin-1-yl)-[1-(6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidin-3-yl]-methanone

HRID 528778Notes

Reaction equation

HRID 528778 reaction equation
C(OC([N:8]1[CH2:34][CH2:33][C:12]2=[C:13]([N:20]3[CH2:23][CH:22]([C:24]([N:26]4[CH2:30][CH2:29][CH:28]([C:31]#[CH:32])[CH2:27]4)=[O:25])[CH2:21]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=O)(C)(C)C.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[C:31]([CH:28]1[CH2:29][CH2:30][N:26]([C:24]([CH:22]2[CH2:21][N:20]([C:13]3[N:14]4[C:18]([N:19]=[C:11]5[CH2:10][CH2:9][NH:8][CH2:34][CH2:33][C:12]=35)=[CH:17][CH:16]=[N:15]4)[CH2:23]2)=[O:25])[CH2:27]1)#[CH:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 8666717710-[3-(3-Ethynyl-pyrrolidine-1-carbonyl)-azetidin-1-yl]-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohept[f]indene-7-carboxylic acid tert-butyl ester

Product 1

HCID 86667178(3-Ethynyl-pyrrolidin-1-yl)-[1-(6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidin-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 36 mg (0.08 mmol) 10-[3-(3-Ethynyl-pyrrolidine-1-carbonyl)-azetidin-1-yl]-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohept[f]indene-7-carboxylic acid tert-butyl ester in 10 mL DCM was added 0.4 mL TFA and stirring was continued for 3 h at room temperature. After addition of 2 mL of MeOH 2M NaOH added drop wise to neutralize the reaction mixture. The solvents were evaporated and the residue was purified by HPLC.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-a5b2761bf08f4bd2baff370e40231e0b
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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