HCID 75204432, compound → HCID 75204433, compound

HRID 1755253Notes

Reaction equation

HRID 1755253 reaction equation
[C:1]1([N:10]2[CH2:14][CH2:13][C@H:12]([NH:15][C:16]([C:18]3[N:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][N:19]=3)=[O:17])[CH2:11]2)[C:2]2[N:3]([CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:5][N:6]=1>CO.[Pd]>[CH2:24]([C:21]1[CH:20]=[N:19][C:18]([C:16]([NH:15][C@H:12]2[CH2:13][CH2:14][N:10]([C:1]3[C:2]4[N:3]([CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:5][N:6]=3)[CH2:11]2)=[O:17])=[N:23][CH:22]=1)[CH3:25]

Participants

4

Reactant 1

HCID 75204432HCID 75204432, compound

Product 1

HCID 75204433HCID 75204433, compoundYield 208.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)—N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)-5-vinylpyrimidine-2-carboxamide (0.04 g, 0.12 mmol, 1 eq) in 1 mL of MeOH was added 10% Pd/C (0.013 g, 0.01 mmol, 0.1 eq). The reaction mixture was equipped with a H2 balloon and stirred for 1 hr at room temperature. The contents were filtered and the purified by HPLC to afford (S)-5-ethyl-N-(1-(pyrrolo[1,2-a]pyrazin-1-yl)pyrrolidin-3-yl)pyrimidine-2-carboxamide (0.009 g, 0.25 mmol, 22%). 1H NMR (400 MHz, CD3OD) δ 8.80 (s, 2 H), 7.76 (m, 1 H), 7.71 (d, J=5.8 Hz, 1 H), 7.54 (s, 1 H), 6.92 (dd, J=2.6, 4.4 Hz, 1 H), 6.84 (d, J=5.5 Hz, 1 H), 5.00-3.60 (br, 5 H), 2.81 (q, J=7.4 Hz, 2 H), 2.65-2.30 (br, 2 H), 1.33 (t, J=7.4 Hz, 3 H); MS: (ES) m/z calculated for C17H18N6O [M+H]+337.2, found 337.

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-55a2c64888534698b6d0add2421b6fe8
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

Loading…