HCID 66853945, compound → HCID 66855190, compound

HRID 876356Notes

Reaction equation

HRID 876356 reaction equation
C(OC([N:11]1[CH2:15][CH:14]([O:16][C:17](=[O:19])[CH3:18])[CH2:13][CH:12]1[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=2)[NH:23][C:22]=1[C:31]1[NH:32][C:33]2[C:38]([C:39]=1[CH2:40][CH:41]1[CH2:45][CH:44]([O:46][C:47](=[O:49])[CH3:48])[CH2:43][N:42]1C(OCC1C=CC=CC=1)=O)=[CH:37][CH:36]=[C:35]([F:60])[CH:34]=2)=O)C1C=CC=CC=1>[Pd].CCOC(C)=O.CO>[C:17]([O:16][CH:14]1[CH2:15][NH:11][CH:12]([CH2:20][C:21]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[NH:23][C:22]=2[C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH2:40][CH:41]2[NH:42][CH2:43][CH:44]([O:46][C:47](=[O:49])[CH3:48])[CH2:45]2)=[CH:37][CH:36]=[C:35]([F:60])[CH:34]=3)[CH2:13]1)(=[O:19])[CH3:18]

Participants

4

Reactant 1

HCID 66853945HCID 66853945, compound

Product 1

HCID 66855190HCID 66855190, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A suspension containing 9 (35 g, 42.7 mmol) in 1:1 EtOAc/MeOH (400 mL) was distributed into two 500 mL Parr bottles (ca. 200 mL/each), and charged with 10% Pd-on-C (wet, 5000 mg/each, Aldrich®). The reaction mixture was pressurized to 50 PSI H2 and shaken for 3 h. The reaction mixture was filtered through a pad of Celite® and the solids were washed with EtOAc. The clarified filtrate was concentrated in vacuo to afford 24 g of 10 as an off-white solid which was used directly in the next reaction. 1H NMR (300 MHz, CDCl3): δ13.10 (br s, 2H) 7.45 (dd, J=5.2, 8.9 Hz, 2H), 7.03 (dd, J=2.3, 9.8 Hz, 2H), 6.85 (m, 2H), 5.35 (m, 2H), 3.71 (m, 2H), 3.18-3.35 (m, 4H), 2.90-3.14 (m, 4H), 2.56 (m, 2H), 2.00-2.10 (m, 2H), 2.04 (s, 6H), 1.80-1.92 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3): δ171.3, 161.7, 158.6, 136.1, 135.9, 130.5, 130.4, 125.4, 119.1, 118.9, 109.6, 108.0, 107.6, 97.6, 97.5, 75.1, 57.7, 51.6, 38.7, 32.8, 21.6 ppm. Mass spectrum (ESI), m/z 550.9 [(M)+; calcd for C30H32F2N4O4: 550.6].

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washthe solids were washed with EtOAc
  3. concentrationThe clarified filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f9ed5e0809bd481b958652fc2d9e85d6
Source dataset
uspto-grants-2015_03
Patent number
US08986993B2

Reaction notes

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