HCID 67606716, compound → HCID 67606764, compound

HRID 1965214Notes

Reaction equation

HRID 1965214 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH:13]2[N:26]([C:29](=[O:49])[CH:30]([NH:35][C:36](=[O:48])[CH:37]([N:39]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH3:40])[CH3:38])[C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:27][CH2:28][CH:12]12)=O)C1C=CC=CC=1>CO.[Pd]>[C:44]([O:43][C:41](=[O:42])[N:39]([CH:37]([C:36](=[O:48])[NH:35][CH:30]([C:29]([N:26]1[CH2:27][CH2:28][CH:12]2[NH:11][CH2:15][CH:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=3)[CH:13]12)=[O:49])[C:31]([CH3:33])([CH3:34])[CH3:32])[CH3:38])[CH3:40])([CH3:45])([CH3:46])[CH3:47]

Participants

4

Reactant 1

HCID 67606716HCID 67606716, compound

Product 1

HCID 67606764HCID 67606764, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of carbamate 83 (546 mg, 0.8 mmol) in MeOH (15 mL) was treated with 10% Pd/C (wet, 208 mg) and subjected to H2 (50 psi) using a Parr apparatus. After 2.5 h, the reaction mixture was filtered through a filter disc (Acrodisc®, PSF—0.45 μM) with MeOH and concentrated to afford amine 84 (443 mg) as a light yellow-colored foam which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.07 (app q, J=9.6 Hz, 1H), 6.89-6.82 (m, 1H), 6.72-6.68 (m, 1H), 4.72-4.69 (m, 1H), 4.56 (d, J=9.3 Hz, 1H), 4.45 (dd, J=2.1, 6.0 Hz, 1H), 4.25-4.11 (m, 4H), 3.90-3.81 (m, 1H), 3.47-3.36 (m, 1H), 3.30-3.24 (m, 1H), 2.79 (s, 3H), 2.46-2.38 (m, 1H), 2.26-2.17 (m, 1H), 1.48 (s, 9H), 1.30 (d, J=6.9 Hz, 3H), 0.99 (s, 9H) ppm. Mass spectrum, m/z [553.7] (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through a filter disc (Acrodisc®, PSF—0.45 μM) with MeOH
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2b515116dfa4484d8ef85450fdc157fc
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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