HCID 86708775, compound → HCID 67682387, compound

HRID 1751568Notes

Reaction equation

HRID 1751568 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:67]([CH3:69])[CH3:68])[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([C:29]2[CH:34]=[CH:33][C:32]([C:35]4[NH:39][C:38]([C@@H:40]5[CH2:44][CH2:43][CH2:42][N:41]5[C:45]([C@H:47]5[C:56]6[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=6)[CH2:50][CH2:49][N:48]5C(OCC5C=CC=CC=5)=O)=[O:46])=[N:37][CH:36]=4)=[CH:31][CH:30]=2)[CH:23]=[CH:22]3)=[CH:17][N:18]=1)=[O:8])=[O:4]>C(O)C.[Pd]>[CH3:68][CH:67]([CH3:69])[C@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[C:7](=[O:8])[N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[NH:15][C:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[NH:39][C:38]([C@@H:40]6[CH2:44][CH2:43][CH2:42][N:41]6[C:45]([C@H:47]6[C:56]7[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=7)[CH2:50][CH2:49][NH:48]6)=[O:46])=[N:37][CH:36]=5)=[CH:31][CH:30]=4)[CH:25]=3)[CH:20]=2)=[CH:17][N:18]=1

Participants

4

Reactant 1

HCID 86708775HCID 86708775, compound

Product 1

HCID 67682387HCID 67682387, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-Benzyl 1-((S)-2-(5-(4-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (137 mg, 0.148 mmol) was dissolved in ethyl alcohol (5 mL) and under Argon charged with 10% Pd/C (79 mg, 0.074 mmol) in a round bottom flask. The flask was then sealed with a rubber septa and the air was removed by vacuum and replaced with H2 from a balloon. This process repeated three times and the mixture was stirred under H2 atmosphere for 18 hours. The resulting mixture was then passed through a celite plug and concentrated down on rotovap. (117 mg, 99%).

Workup

  1. customThe flask was then sealed with a rubber septa
  2. customthe air was removed by vacuum
  3. concentrationconcentrated down on rotovap

Sources & evidence

ORD record
ord-d6c8d39536c84b2f99c3a6e331613b0f
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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