Acetonitrile → (3S*,5R*)-3-Amino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1698366Notes

Reaction equation

HRID 1698366 reaction equation
[CH:1]1([NH:4][CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:7]=2)[CH2:3][CH2:2]1.[C:20]([O:24][C:25]([N:27]1[CH2:34][CH:33]2[CH2:35][CH:29](C(=O)[O:31][C:32]2=O)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].CC#[N:40]>>[C:20]([O:24][C:25]([N:27]1[CH2:34][C@H:33]([C:32](=[O:31])[N:4]([CH:1]2[CH2:2][CH2:3]2)[CH2:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[CH:7]=2)[CH2:35][C@H:29]([NH2:40])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 6342Acetonitrile3×HCID 59778297Tert-butyl 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylateHCID 59817701cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-amine

Product 1

HCID 69071766(3S*,5R*)-3-Amino-5-{cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

The title compound is prepared analogously as described in Example 152A using cyclopropyl-[1-(3-methoxy-propyl)-1H-indol-3-ylmethyl]-amine and 2,4-Dioxo-3-oxa-7-aza-bicyclo[3.3.1]nonane-7-carboxylic acid tert-butyl ester. MS: 485 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 3.09 min.

Workup

  1. custom3.09 min.

Sources & evidence

ORD record
ord-ff482eba504246babf87dfc27d9b60d9
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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