Acetic Acid → HCID 59239439, compound

HRID 1698025Notes

Reaction equation

HRID 1698025 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][C@@H:35]4[CH3:40])[C:25]4[CH2:31][CH2:30][N:29]([CH:32]=[O:33])[CH2:28][C:26]=4[N:27]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.CO.C(O)(=O)C>[Pd]>[CH3:40][C@@H:35]1[N:34]([C:24]2[C:25]3[CH2:31][CH2:30][N:29]([CH:32]=[O:33])[CH2:28][C:26]=3[N:27]=[C:22]([C:19]3[CH:18]=[CH:17][C:16]([NH:15][C:13]4[NH:14][C:9](=[O:8])[CH:10]=[CH:11][CH:12]=4)=[CH:21][CH:20]=3)[N:23]=2)[CH2:39][CH2:38][O:37][CH2:36]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 59239634HCID 59239634, compound

Product 1

HCID 59239439HCID 59239439, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
40 °C

Procedure

(S)-2-(4-(6-(benzyloxy)pyridin-2-ylamino)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carbaldehyde (0.066 g, 0.00012 mol), Palladium on Carbon 10% (0.1:0.9, Palladium:carbon black, 0.094 g), dry Methanol (3.30 mL, 0.0815 mol) and Acetic acid (0.21 mL, 0.0037 mol) were combined under nitrogen then purged with hydrogen, heated at 40° C., and stirred overnight. The reaction mixture was purged with nitrogen, added celite, filtered through celite, concentrated, and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 10.23 (s, 1H), 9.14 (s, 1H), 8.31-8.16 (m, 3H), 7.76 (s, 2H), 7.42 (t, J=7.8, 1H), 6.31 (s, 1H), 6.00 (d, J=8.1, 1H), 4.69-4.39 (m, 2H), 4.07 (d, J=5.4, 2H), 3.89 (d, J=11.1, 1H), 3.75-3.38 (m, 4H), 3.18 (d, J=4.4, 2H), 2.74 (s, 1H), 2.66 (d, J=12.1, 1H), 1.27 (t, J=6.4, 3H). LC/MS-m/z+447.2 (M+H)+.

Workup

  1. customthen purged with hydrogen
  2. customThe reaction mixture was purged with nitrogen
  3. additionadded celite
  4. filtrationfiltered through celite,
  5. concentrationconcentrated
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-295ea07b25f047ce80fc738c69e71cbc
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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