HCID 73387047, compound → HCID 73387048, compound

HRID 1400729Notes

Reaction equation

HRID 1400729 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:38]([CH3:39])=[N:37][C:36]2=[CH:40][C:33]3=[N:34][N:35]2[C:11]=1[N:12]1[CH2:43][CH2:42][C:15]([CH3:44])([O:16][CH2:17][CH:18]=[CH:19][CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[CH:41]=[C:32]3[CH:31]=[CH:30][CH:29]=2)[CH2:14][CH2:13]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C@@H:6]([C:10]1[C:38]([CH3:39])=[N:37][C:36]2=[CH:40][C:33]3=[N:34][N:35]2[C:11]=1[N:12]1[CH2:13][CH2:14][C:15]([CH3:44])([O:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[CH:41]=[C:32]3[CH:31]=[CH:30][CH:29]=2)[CH2:42][CH2:43]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 73387047HCID 73387047, compound

Product 1

HCID 73387048HCID 73387048, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of example 20 (30 mg, 0.050 mmol), 10% Pd/C (5.35 mg, 5.03 μmol) in MeOH was stirred under a H2 balloon for 3 h. It was then filtered and concentrated to obtain 28 mg (93%) of the desired product as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.51 (br. s., 1H), 7.70 (d, J=7.1 Hz, 1H), 7.54 (t, J=7.6 Hz, 1H), 7.47 (d, J=7.3 Hz, 1H), 7.40 (d, J=6.6 Hz, 1H), 7.34 (t, J=7.2 Hz, 1H), 7.04 (d, J=7.1 Hz, 2H), 6.81 (s, 1H), 6.01 (br. s., 1H), 4.59 (t, J=11.9 Hz, 1H), 4.13 (br. s., 2H), 3.91 (t, J=11.5 Hz, 1H), 3.53 (d, J=3.5 Hz, 1H), 3.42 (d, J=4.9 Hz, 2H), 2.84 (d, J=9.9 Hz, 1H), 2.63 (br. s., 3H), 2.36 (br. s., 1H), 2.16 (br. s., 1H), 2.10-2.02 (m, 1H), 1.93 (d, J=12.5 Hz, 1H), 1.80 (d, J=9.0 Hz, 2H), 1.70-1.54 (m, 2H), 1.36-1.20 (m, 12H). LCMS (M+1)=599.38.

Workup

  1. filtrationIt was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9fb56a0f057246ac9b57a229f5ea5eb8
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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