(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → 1-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride

HRID 2173320Notes

Reaction equation

HRID 2173320 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[C@H:16]12[CH2:22][C@H:19]([NH:20][CH2:21]1)[CH2:18][N:17]2C(OC(C)(C)C)=O.[ClH:30].N1(C(=O)CC2C=NC(N3C=NN=N3)=CC=2)CCNCC1>>[ClH:30].[C@H:16]12[CH2:22][C@H:19]([NH:20][CH2:21]1)[CH2:18][N:17]2[C:13](=[O:15])[CH2:12][C:9]1[CH:10]=[N:11][C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 66524945[6-(1H-Tetrazol-1-yl)pyridine-3-yl]acetic acidHCID 675171491-(piperazin-1-yl)-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride

Product 1

HCID 866930151-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride

Procedure

1-[(1S,4S)-2,5-Diazabicyclo[2.2.1]hept-2-yl]-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride was prepared in two steps starting from [6-(1H-tetrazol-1-yl)pyridin-3-yl]acetic acid and commercially available tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate in an analogous fashion as described for the synthesis of 1-(piperazin-1-yl)-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride. MS m/z 286 (M+1)+.

Sources & evidence

ORD record
ord-25ec77aa6b6e4e449b5d4ffd2f0a18cf
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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