HCID 69320502, compound → HCID 11313604, compound

HRID 2114610Notes

Reaction equation

HRID 2114610 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[C:8]([C:16]3[NH:20][C:19]4[CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=[CH:24][C:18]=4[N:17]=3)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CN1C(=O)CCC1>[NH2:25][C:22]1[CH:23]=[CH:24][C:18]2[N:17]=[C:16]([C:8]3[C:9]4[C:14]([NH2:15])=[N:13][CH:12]=[N:11][C:10]=4[N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:7]=3)[NH:20][C:19]=2[CH:21]=1

Participants

5

Reactant 2

HCID 69320502HCID 69320502, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11313604HCID 11313604, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7-Cyclopentyl-5-(6-nitro-1H-benzoimidazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1E, 1.0 g) was combined with 10% Palladium on carbon (100 mg) in 50 mL of anhydrous NMP and subjected to 50 psi of hydrogen at room temperature for 24 hours. LCMS monitor suggested pure desired product (M/Z 333.5, retention time 0.70 min. with analytical HPLC method 4). The mixture was filtered through celite. Desired product was used as an NMP stock solution (concentration of about 0.92 g in 45 mL).

Sources & evidence

ORD record
ord-373af516af974060a6ac8d4d532569a7
Source dataset
uspto-grants-2008_10
Patent number
US07435739B2

Reaction notes

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