2-(4-(2-(3-((Benzyloxycarbonylamino)methyl)-4-(ethylsulfonyl)phenylamino)-2-oxoethoxy)-3,5-dimethylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid → 2-(4-(2-(3-(Aminomethyl)-4-(ethylsulfonyl)phenylamino)-2-oxoethoxy)-3,5-dimethylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

HRID 735710Notes

Reaction equation

HRID 735710 reaction equation
C(OC([NH:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:24][C:25](=[O:66])[CH2:26][O:27][C:28]2[C:33]([CH3:34])=[CH:32][C:31]([CH:35]([NH:39][C:40]3[CH:41]=[C:42]4[C:47](=[CH:48][CH:49]=3)[C:46]([N:50]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[N:45][CH:44]=[CH:43]4)[C:36]([OH:38])=[O:37])=[CH:30][C:29]=2[CH3:65])[CH:16]=[CH:17][C:18]=1[S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:24][C:25](=[O:66])[CH2:26][O:27][C:28]2[C:29]([CH3:65])=[CH:30][C:31]([CH:35]([NH:39][C:40]3[CH:41]=[C:42]4[C:47](=[CH:48][CH:49]=3)[C:46]([N:50]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C:51]([O:53][C:54]([CH3:55])([CH3:57])[CH3:56])=[O:52])=[N:45][CH:44]=[CH:43]4)[C:36]([OH:38])=[O:37])=[CH:32][C:33]=2[CH3:34])[CH:16]=[CH:17][C:18]=1[S:19]([CH2:22][CH3:23])(=[O:21])=[O:20]

Participants

4

Reactant 1

HCID 578428132-(4-(2-(3-((Benzyloxycarbonylamino)methyl)-4-(ethylsulfonyl)phenylamino)-2-oxoethoxy)-3,5-dimethylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

Product 1

HCID 578427852-(4-(2-(3-(Aminomethyl)-4-(ethylsulfonyl)phenylamino)-2-oxoethoxy)-3,5-dimethylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acidYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 79D (190 mg, 0.205 mmol) in 5 mL methanol, was added 10% Pd—C (30 mg). The reaction was evacuated and flushed with H2 (3×), then stirred under an atmosphere of H2 for 1 h. The reaction was filtered and concentrated to afford 151 mg (93%) of 79E as an orange solid. MS (ESI) m/z 926.5 (M+H)+.

Workup

  1. customThe reaction was evacuated
  2. customflushed with H2 (3×)
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e7e8457d4b4404d928cbacdbc97a102
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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