HCID 86691444, compound → HCID 71255583, compound

HRID 540331Notes

Reaction equation

HRID 540331 reaction equation
[N:1]([CH2:4][C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([N:18]2[CH2:24][CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[CH2:19]2)[CH:9]=1)=[O:6])=[N+]=[N-]>CO.[Pd]>[CH2:19]1[C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[CH2:22][CH2:23][CH2:24][N:18]1[C:10]1[CH:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][NH2:1])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 1

HCID 86691444HCID 86691444, compound

Product 1

HCID 71255583HCID 71255583, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-azido-N-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]acetamide (65 mg, 0.17 mmol) in methanol was added palladium (10% on carbon, 7 mg). After being stirred at room temperature overnight under a hydrogen atmosphere, the resulting mixture was filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC to afford 30 mg of product as a white powder (yield was 60.5%). MS obsd. (ESI+) [(M+H)+] 347. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (s, 1 H), 7.78 (d, J=8.0 Hz, 1 H), 7.55-7.49 (m, 3 H), 7.23-7.20 (m, 1 H), 7.15-7.08 (m, 3 H), 4.79 (s, 2 H), 4.13 (brs, 2 H), 3.45 (brs, 2 H), 3.04 (brs, 2 H), 1.79 (brs, 2 H).

Workup

  1. filtrationthe resulting mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b6f616e116fd4b5e9d132b294dd4636d
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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