HCID 75204203, compound → HCID 75204311, compound

HRID 1755244Notes

Reaction equation

HRID 1755244 reaction equation
[C:1]1([C:6]2[CH:7]=[N:8][C:9]([C:12]([NH:14][C@H:15]3[CH2:19][CH2:18][N:17]([C:20]4[C:21]5[N:22]([CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:24][N:25]=4)[CH2:16]3)=[O:13])=[N:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:6]2[CH:7]=[N:8][C:9]([C:12]([NH:14][C@H:15]3[CH2:19][CH2:18][N:17]([C:20]4[C:21]5[N:22]([CH:26]=[CH:27][CH:28]=5)[CH:23]=[CH:24][N:25]=4)[CH2:16]3)=[O:13])=[N:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 75204203HCID 75204203, compound

Product 1

HCID 75204311HCID 75204311, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-5-(cyclopent-1-en-1-yl)-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.07 g, 0.19 mmol, 1 eq) in 1 mL of MeOH was added 10% Pd/C (0.02 g, 0.02 mmol, 0.1 eq). The reaction mixture was equipped with a H2 balloon and stirred for 3 hr at room temperature. The contents were filtered and the purified by HPLC to afford (S)-5-cyclopentyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.005 g, 0.013 mmol, 7%). 1H NMR (400 MHz, CD3OD) δ 8.83 (s, 2 H), 7.78 (q, J=1.1 Hz, 1 H), 7.73 (d, J=5.8 Hz, 1 H), 7.57 (d, J=3.9 Hz, 1 H), 6.94 (dd, J=2.7, 4.7 Hz, 1 H), 6.86 (d, J=5.9 Hz, 1 H), 5.00-4.80 (m, 1 H), 4.50-3.50 (br, 4 H), 3.20-3.10 (m, 1H), 2.60-2.48 (m, 1 H), 2.48-2.38 (br, 1 H), 2.22-2.12 (m, 2 H), 1.95-1.60 (m, 6 H); MS: (ES) m/z calculated for C21H24N6O [M+H]+ 377.2, found 377.

Workup

  1. customThe reaction mixture was equipped with a H2 balloon
  2. filtrationThe contents were filtered
  3. customthe purified by HPLC

Sources & evidence

ORD record
ord-7e33c817bb2c4ce491e60d52dd22d93a
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

Loading…