HCID 66808398, compound → HCID 60204790, compound

HRID 883968Notes

Reaction equation

HRID 883968 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[N:11][CH:10]=[N:9][C:8]=2[N:31]=1)([CH3:3])[CH3:2]>C(O)(=O)C.CO.[Pd]>[NH2:20][C:18]1[CH:17]=[CH:16][C:15]([S:23][C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)=[C:14]([NH:13][C:12]2[C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:31][C:8]=3[N:9]=[CH:10][N:11]=2)[CH:19]=1

Participants

5

Reactant 1

HCID 66808398HCID 66808398, compound

Product 1

HCID 60204790HCID 60204790, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A slurry of the compound prepared in Example 67A (0.7 g, 1.73 mmol) and 10% Pd/C (100 mg) in acetic acid (10 ml) and methanol (10 mL) was placed under a hydrogen balloon atmosphere with stirring for 20 hours at room temperature. The slurry was filtered and the solvent removed under vacuum to provide the title compound as an acetic acid salt (540 mg, 63%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.35 (d, J=7.0 Hz, 6H), 1.91 (s, 6H), 3.27 (m, 1H), 6.55 (d, J=8.8 Hz, 2H), 6.62 (m, 1H), 6.69 (m, 1H), 6.95 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.5 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 7.95 (s, 1H), 8.75 (s, 1H), 8.99 (m, 1H), 9.52 (s, 1H), 11.57 (bs, 1H); MS (ESI+) m/z 404 (M+H)+.

Workup

  1. filtrationThe slurry was filtered
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-68c619367da541de97512e246d87a07a
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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