HCID 59129228, compound → HCID 59129353, compound

HRID 1847871Notes

Reaction equation

HRID 1847871 reaction equation
[N:1]([CH2:4][C@H:5]([OH:37])[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]([C:19]3([C:22]4[CH:32]=[CH:31][C:25]5[O:26][C:27]([F:30])([F:29])[O:28][C:24]=5[CH:23]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:33]([CH3:36])([CH3:35])[CH3:34])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@H:5]([OH:37])[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]([C:19]3([C:22]4[CH:32]=[CH:31][C:25]5[O:26][C:27]([F:30])([F:29])[O:28][C:24]=5[CH:23]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:33]([CH3:35])([CH3:34])[CH3:36]

Participants

4

Reactant 1

HCID 59129228HCID 59129228, compound

Product 1

HCID 59129353HCID 59129353, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution (R)—N-(1-(3-azido-2-hydroxypropyl)-2-tert-butyl-1H-indol-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (2.4 g, 4.0 mmol) in MeOH (25 mL) was added 5% Pd/C (2.4 g) under a Hydrogen gas filled balloon. After 18 h, the reaction mixture was filtered through celite and rinsed with 300 mL ethyl acetate. The organic layer was washed with 1 N HCl and evaporated to give (S)—N-(1-(3-amino-2-hydroxypropyl)-2-tert-butyl-1H-indol-5-yl)-1-(2,2-difluoro-benzo[d][1,3]-dioxol-5-yl)cyclopropane-carboxamide (1.37 g). MS (M+1)=486.5.

Workup

  1. additionfilled balloon
  2. filtrationthe reaction mixture was filtered through celite
  3. washrinsed with 300 mL ethyl acetate
  4. washThe organic layer was washed with 1 N HCl
  5. customevaporated

Sources & evidence

ORD record
ord-a56643a80e5b4767b49cc297658b9364
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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