(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → tert-butyl (1S,4S)-5-{[1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 2391627Notes

Reaction equation

HRID 2391627 reaction equation
CS(O[CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]=[CH:14][N:15]([C:16]3[S:17][C:18]([C:34](=[O:36])[NH2:35])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=3)[C:9]=2[CH:8]=1)(=O)=O.[C@H:37]12[CH2:43][C@H:40]([NH:41][CH2:42]1)[CH2:39][N:38]2[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45]>ClCCl>[C:34]([C:18]1[S:17][C:16]([N:15]2[C:9]3[CH:8]=[C:7]([CH2:6][N:41]4[CH2:42][C@@H:37]5[CH2:43][C@H:40]4[CH2:39][N:38]5[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[N:12]=[CH:11][C:10]=3[N:13]=[CH:14]2)=[CH:20][C:19]=1[O:21][C@@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]([F:32])([F:33])[F:31])[CH3:23])(=[O:36])[NH2:35]

Participants

4

Reactant 2

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 86647102[1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoro-methyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate

Product 1

HCID 86647109tert-butyl (1S,4S)-5-{[1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

108 mg of [1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate are dissolved in 2.5 ml dichloromethane. Under N2 atmosphere tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (198 mg) is added. The reaction mixture is stirred at 40° C. for 1 hour and then concentrated to dryness under vacuum. The residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v)) to obtain tert-butyl (1S,4S)-5-{[1-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-1H-imidazo[4,5-c]pyridin-6-yl]methyl}-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. customThe residue is purified by preparative HPLC (ammonium formate buffer/acetonitrile, elution gradient 97/3 to 0/100 (v/v))

Sources & evidence

ORD record
ord-5b7f883e154a4575b11856b22196c03b
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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