HCID 86658348, compound → HCID 44196976, compound

HRID 340111Notes

Reaction equation

HRID 340111 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][C@@H:29]([OH:33])[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][C@@H:29]([OH:33])[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 86658348HCID 86658348, compound

Product 1

HCID 44196976HCID 44196976, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% w/w Pd/C (1 mg) was added to a solution of N-((S)-1-azido-3-(2,4-dichlorophenyl)propan-2-yl)-5-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxamide (4.0 mg, 0.008 mmol) in MeOH (0.5 mL). The solution was put under vacuum and purged with H2 (3×). The reaction mixture was then 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 then concentrated to yield N-((S)-1-amino-3-(2,4-dichlorophenyl)propan-2-yl)-5-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)thiophene-2-carboxamide as a solid (3.7 mg, 98%). m/z 477 (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), 5.22-5.17 (m, 1H), 4.59-4.50 (m, 1H), 3.87-3.77 (m, 1H), 3.19-2.84 (m, 5H), 2.33-2.26 (m, 1H), 1.88-1.82 (m, 1H), 1.13 (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-792ab7b337f2435cb6a24460e3b124d4
Source dataset
uspto-grants-2014_11
Patent number
US08895566B2

Reaction notes

Loading…