HCID 58204696, compound → HCID 58204358, compound

HRID 1629543Notes

Reaction equation

HRID 1629543 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:40]=[CH:39][C:20]3[C:21]4[N:25]([CH2:26][CH2:27][O:28][C:19]=3[CH:18]=2)[CH:24]=[C:23]([C:29]2[N:30]([CH2:34][C:35]([F:38])([F:37])[F:36])[N:31]=[CH:32][N:33]=2)[N:22]=4)[C@H:13]([C:41](=[O:43])[NH2:42])[CH2:12]1)=O)C1C=CC=CC=1>[Pd]>[F:37][C:35]([F:36])([F:38])[CH2:34][N:30]1[C:29]([C:23]2[N:22]=[C:21]3[C:20]4[CH:39]=[CH:40][C:17]([N:14]5[CH2:15][CH2:16][NH:11][CH2:12][C@H:13]5[C:41]([NH2:42])=[O:43])=[CH:18][C:19]=4[O:28][CH2:27][CH2:26][N:25]3[CH:24]=2)=[N:33][CH:32]=[N:31]1

Participants

3

Reactant 1

HCID 58204696HCID 58204696, compound

Product 1

HCID 58204358HCID 58204358, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (S)-3-carbamoyl-4-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl}-piperazine-1-carboxylic acid benzyl ester (0.03 g) and 10% Pd/C (0.014 g) in IMS (5 mL) was stirred under an atmosphere of hydrogen at RT for 64 h. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 20% methanol in DCM) to give 543 (0.005 g, 20%). LCMS: RT=2.49 min, [M+H]+463. 1H NMR 400 MHz (MeOD): δ 8.28 (1 H, d, J=9.03 Hz), 8.00 (1 H, s), 7.78 (1 H, s), 6.79 (1 H, dd, J=9.09, 2.63 Hz), 6.56 (1 H, d, J=2.58 Hz), 5.83 (2 H, q, J=8.50 Hz), 4.50-4.43 (3 H, m), 4.30 (1 H, t, J=3.89 Hz), 3.52-3.45 (2 H, m), 3.38 (1 H, dd, J=13.28, 3.28 Hz), 3.34 (1 H, s), 3.13-3.10 (2 H, m), 2.96-2.88 (1 H, m)

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f6c3a3e907784efb98000e6715769008
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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