HCID 136504501, compound → HCID 136504489, compound

HRID 1507507Notes

Reaction equation

HRID 1507507 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)=[N:12][C:11]=1[NH:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]1>[C].[Pd].CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[N:12][C:11]=1[NH:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]1

Participants

4

Reactant 1

HCID 136504501HCID 136504501, compound

Product 1

HCID 136504489HCID 136504489, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Into a 10-mL round-bottom flask purged and maintained with an atmosphere of hydrogen, was placed a solution of benzyl 4-[5-(1,3-benzothiazol-2-yl)-4-[[(3R)-1-[(tert-butoxy)carbonyl]piperidin-3-yl]amino]-6-oxo-1,6-dihydropyrimidin-2-yl]piperidine-1-carboxylate (644 mg, 1.00 mmol, 1.00 equiv), Palladium carbon (64.4 mg) and methanol (20 mL). The resulting mixture was stirred overnight at room temperature. Filtration and evaporation gave 480 mg (94%) of the title compound as a light yellow solid, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 511.

Workup

  1. customInto a 10-mL round-bottom flask purged
  2. temperaturemaintained with an atmosphere of hydrogen
  3. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-c839d8c0c9f2442b8a0a494954e18719
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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