HCID 86726231, compound → HCID 11193703, compound

HRID 1174331Notes

Reaction equation

HRID 1174331 reaction equation
[CH3:1][C:2]([CH3:62])([CH3:61])[C@H:3]([N:45]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([N+:57]([O-])=O)[CH:52]=2)[C:46]1=[O:60])[C:4]([NH:6][C@@H:7]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@@H:8]([OH:37])[CH2:9][C@@H:10]([NH:24][C:25]([C@@H:27]([NH:32][C:33](=[O:36])[O:34][CH3:35])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)=[O:5]>C(O)C.[Pd]>[NH2:57][C:53]1[CH:52]=[C:51]([CH:56]=[CH:55][CH:54]=1)[CH2:50][N:47]1[CH2:48][CH2:49][N:45]([C@@H:3]([C:2]([CH3:61])([CH3:1])[CH3:62])[C:4]([NH:6][C@@H:7]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:8]([OH:37])[CH2:9][C@@H:10]([NH:24][C:25]([C@@H:27]([NH:32][C:33](=[O:36])[O:34][CH3:35])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:16][CH:17]=2)=[O:5])[C:46]1=[O:60]

Participants

4

Reactant 1

HCID 86726231HCID 86726231, compound

Product 1

HCID 11193703HCID 11193703, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 125C (0.077 g, 0.091 mmol) in ethanol (2 mL) was treated with 10% Pd on carbon (0.029 g), stirred under an atmosphere of hydrogen (balloon pressure) at 25° C. for 3 hours, filtered and concentrated under reduced pressure. The residue was purified by reversed phase chromatography on a C18 column eluting with 5-100% acetonitrile in water (0.1% TFA. The product was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (0.035 g, 47% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.83(s, 9H), 0.89(s, 9H), 1.60-1.49(m, 2H), 2.38-2.28(m, 1H), 2.62-2.53(m, 1H), 2.68-2.66(m, 2H), 2.86-2.76(m, 2H), 2.98-2.89(q, J=9.19 Hz, 1H), 3.20-3.14(m, 1H), 3.50(s, 3H), 3.70-3.62(m, 1H), 3.86-3.83(d, J=9.93 Hz, 1H), 4.07(s, 1H), 4.14(s, 2H), 4.25-4.10(m, 2H), 4.55-4.53(d, J=7.35 Hz, 1H), 5.03(s, 2H), 6.42-6.39(d, J=7.35 Hz, 1H), 6.48-6.66(m, 2H), 6.62-6.59(d, J=9.93 Hz, 1H), 7.01-6.96(t, J=7.91 Hz, 1H), 7.11-7.04(m, 5H), 7.24-7.21(d, J=8.09 Hz, 2H), 7.33-7.28(m, 1H), 7.40-7.37(d, J=9.19 Hz, 1H), 7.91-7.80(m, 5H), 8.64-8.63(d, J=4.41 Hz, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reversed phase chromatography on a C18 column
  4. washeluting with 5-100% acetonitrile in water (0.1% TFA
  5. customThe product was partitioned between ethyl acetate and saturated NaHCO3
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-413d07fc1aac48108fc29087e2208454
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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