HCID 91042424, compound → HCID 11170370, compound

HRID 1174353Notes

Reaction equation

HRID 1174353 reaction equation
[N+:1]([C:4]1[C:62]([CH3:63])=[CH:61][CH:60]=[CH:59][C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:13]([NH:15][C@@H:16]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:17]([OH:46])[CH2:18][C@@H:19]([NH:33][C:34]([C@@H:36]([NH:41][C:42](=[O:45])[O:43][CH3:44])[C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:23][CH:22]=2)=[O:14])[C:8]1=[O:58])([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[C:62]([CH3:63])=[CH:61][CH:60]=[CH:59][C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([C:54]([CH3:55])([CH3:56])[CH3:57])[C:13]([NH:15][C@@H:16]([CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:17]([OH:46])[CH2:18][C@@H:19]([NH:33][C:34]([C@@H:36]([NH:41][C:42](=[O:45])[O:43][CH3:44])[C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:23][CH:22]=2)=[O:14])[C:8]1=[O:58]

Participants

5

Reactant 2

HCID 91042424HCID 91042424, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11170370HCID 11170370, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of Example 141E (64 mg, 0.074 mmol) in ethanol (2 mL) was treated with 10% Pd/C (23.6 mg, 0.022 mmol) with a hydrogen balloon at 25° C. for 16 h. The catalyst was filtered through Celite®, rinsed with ethanol, and the solvents were evaporated. The crude residue was purified using reverse phase chromatography eluting with a gradient of 95% water (0.1% trifluoroacetic acid)/5% acetonitrile to 100% acetonitrile to give the title compound (0.051 g, 83%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.83(s, 9H), 0.87(s, 9H), 1.58-1.49(m, 2H), 2.12(s, 3H), 2.23-2.12(m, 1H), 2.61-2.54(m, 1H), 2.66-2.64(d, J=7.35 Hz, 2H), 2.88-2.81(m, 2H), 3.02-2.93(q, J=8.58 Hz, 1H), 3.18-3.12(m, 1H), 3.48(s, 3H), 3.69-3.65(m, 1H), 3.86-3.82(d, J=9.93 Hz, 1H), 4.05(s, 1H), 4.33-4.13(m, 4H), 6.65-6.58(m, 2H), 6.99-6.90(m, 4H), 7.08-7.05(d, J=7.72 Hz, 2H), 7.28-7.25(d, J=8.46 Hz, 2H), 7.37-7.33(d, J=9.93 H, 1H), 7.46-7.42(m, 1H), 7.90-7.83(m, 2H), 8.03-7.90(m, 2H), 8.69-8.67(d, J=4.78 Hz, 1H).

Workup

  1. filtrationThe catalyst was filtered through Celite®
  2. washrinsed with ethanol
  3. customthe solvents were evaporated
  4. customThe crude residue was purified
  5. washeluting with a gradient of 95% water (0.1% trifluoroacetic acid)/5% acetonitrile to 100% acetonitrile

Sources & evidence

ORD record
ord-626c359fa13e4fd0b8d5406b7a1bf5fa
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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