HCID 46883308, compound → HCID 69199992, compound

HRID 2223153Notes

Reaction equation

HRID 2223153 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][CH:19]=[N:20][C:13]=3[N:12]=[C:11]2[C@H:21]([N:23]([CH:38]2[CH2:43][CH2:42][N:41]([CH:44]([CH3:46])[CH3:45])[CH2:40][CH2:39]2)[C:24](=[O:37])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=2)[CH3:22])=[CH:6][CH:5]=1)[CH3:2]>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][NH:20][C:13]=3[N:12]=[C:11]2[C@H:21]([N:23]([CH:38]2[CH2:43][CH2:42][N:41]([CH:44]([CH3:45])[CH3:46])[CH2:40][CH2:39]2)[C:24](=[O:37])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([C:33]([F:35])([F:34])[F:36])[CH:27]=2)[CH3:22])=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 46883308HCID 46883308, compound

Product 1

HCID 69199992HCID 69199992, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

F2 (665 mg, 1.09 mmol) was dissolved in methanol and degassed with nitrogen for 5 min. Palladium (10% wt. on C, 665 mg) was added, then the reaction was placed under hydrogen atmosphere with a balloon. The reaction stirred overnight at room temperature, then it was filtered through Celite, and concentrated in vacuo. Purified by reverse-phase HPLC to yield 280 mg of a colorless solid, 5. MS (MH+): 644.5. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.10 (m, 7H), 5.08 (broad s, 1H), 4.70 (dd, 1H, J=11.2, 5.0 Hz), 4.01 (quint, 2H, 6.8 Hz), 3.67 (broad s, 1H), 3.42 (s, 3H), 3.14 (broad s, 3H), 2.67 (broad m, 3H), 2.55 (t, 3H, J=6.2 Hz), 2.29 (broad s, 2H), 1.90 (dd, 3H, J=5.6, 2.5 Hz), 1.39 (t, 6H, J=6.9 Hz), 1.25 (d, 6H, 6.4 Hz) ppm.

Workup

  1. customdegassed with nitrogen for 5 min
  2. additionPalladium (10% wt. on C, 665 mg) was added
  3. filtrationit was filtered through Celite
  4. concentrationconcentrated in vacuo
  5. customPurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a853da8c64b94b2bb3d28f5a19ff7ab4
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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