HCID 86680552, compound → HCID 44196975, compound

HRID 521347Notes

Reaction equation

HRID 521347 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:15][C:16]([C:18]1[S:19][C:20]([C:23]2[C:24]3[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[CH:21][CH:22]=1)=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:15][C:16]([C:18]1[S:19][C:20]([C:23]2[C:24]3[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)=[CH:21][CH:22]=1)=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14]

Participants

4

Reactant 1

HCID 86680552HCID 86680552, compound

Product 1

HCID 44196975HCID 44196975, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (6 mg) was added to a solution of N-((S)-1-azido-3-(2,4-dichlorophenyl)propan-2-yl)-5-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxamide (59 mg, 0.121 mmol) in methanol (2.5 mL). The solution was put under vacuum and purged with H2 (3×), and then the reaction mixture was stirred under a hydrogen atmosphere for 2 hours. LC-MS analysis of the reaction mixture showed no more starting material. The reaction mixture was filtered and concentrated to yield N-((S)-1-amino-3-(2,4-dichlorophenyl)propan-2-yl)-5-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxamide as a foam (53 mg, 95%). m/z 461 (M+); 1H NMR (DMSO d6) δ (ppm) 8.91 (s, 1H), 8.58-8.56 (m, 1H), 7.90 (br s, 2H), 7.84 (d, 1H, J=4.3 Hz), 7.78 (d, 1H, J=4.1 Hz), 7.60 (m, 1H), 7.39-7.33 (m, 2H), 4.55-4.42 (m, 1H), 3.87-3.77 (m, 1H), 3.19-2.84 (m, 6H), 2.33-2.26 (m, 1H), 1.88-1.82 (m, 1H), 1.18 (d, 3H, J=6.9 Hz).

Workup

  1. custompurged with H2 (3×)
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-aeebf88d864041e88a9adc3c17062eae
Source dataset
uspto-grants-2016_05
Patent number
US09328091B2

Reaction notes

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