HCID 58529556, compound → HCID 58529507, compound

HRID 1972828Notes

Reaction equation

HRID 1972828 reaction equation
C([N:8]1[CH2:17][CH2:16][N:15]2[CH:10]([CH2:11][O:12][CH:13]([C:18]3[N:26]4[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]4)=[C:20]([C:28]4[CH:29]=[CH:30][C:31]5[C:35]([CH:36]=4)=[N:34][N:33]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:32]=5)[CH:19]=3)[CH2:14]2)[CH2:9]1)C1C=CC=CC=1>[Pd].CC(O)=O>[CH2:11]1[CH:10]2[CH2:9][NH:8][CH2:17][CH2:16][N:15]2[CH2:14][CH:13]([C:18]2[N:26]3[C:21]([C:22]([NH2:27])=[N:23][CH:24]=[N:25]3)=[C:20]([C:28]3[CH:29]=[CH:30][C:31]4[C:35]([CH:36]=3)=[N:34][N:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:32]=4)[CH:19]=2)[O:12]1

Participants

4

Reactant 1

HCID 58529556HCID 58529556, compound

Product 1

HCID 58529507HCID 58529507, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolvent2×

Procedure

Palladium on carbon (60 mg, 10% by wt.) was placed under an inert atmosphere and suspended in AcOH (5 mL). A solution of 7-(8-benzyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)-5-(2-phenyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (600 mg, 1.08 mmol) in AcOH (6 mL) was added. The reaction mixture was placed under H2 atmosphere (1 Atm pressure) and stirred overnight. Additional amounts of palladium on carbon (10% by wt.) were added as needed until the reaction was complete as observed by HPLC. The resulting mixture was filtered through a pad of Celite® and the solvent was concentrated under reduced pressure. Trituration with Et2O afforded 150 mg (29%) of the desired product as an off-white solid. 1H NMR (300 MHz, DMSO-d6) 9.16 (s, 1 H), 8.10 (d, 2 H), 7.94 (s, 1 H), 7.85 (d, 1 H), 7.68 (s, 1 H), 7.58 (t, 2 H), 7.44 (t, 1 H), 7.21 (dd, 1H), 6.78 (s, 1H), 5.14 (dd, 1H), 3.74 (dd, 1H), 3.49-3.28 (m, 1H), 2.94 (dd, 1H), 2.75-2.60 (m, 5H), 2.46-2.38 (m, 1H), 2.26-2.08 (m, 3H); LC-MS [M+H]+=467, RT=0.91 min.

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite®
  2. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d91505a4fd1b4c61bebc82d624966840
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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