Acetic Acid → HCID 59239328, compound

HRID 1698014Notes

Reaction equation

HRID 1698014 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:35]4[CH2:40][CH2:39][O:38][CH2:37][C@@H:36]4[CH3:41])[C:25]4[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[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]>[C:32]([N:29]1[CH2:30][CH2:31][C:25]2[C:24]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][C@@H:36]3[CH3:41])=[N:23][C:22]([C:19]3[CH:20]=[CH:21][C:16]([NH:15][C:13]4[NH:14][C:9](=[O:8])[CH:10]=[CH:11][CH:12]=4)=[CH:17][CH:18]=3)=[N:27][C:26]=2[CH2:28]1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 67177278HCID 67177278, compound

Product 1

HCID 59239328HCID 59239328, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
65 °C

Procedure

Step 2—Synthesis of compound wf: (S)-1-(2-(4-(6-(benzyloxy)pyridin-2-ylamino)phenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethanone (0.098 g, 0.00018 mol), Palladium on Carbon 10% (0.1:0.9, Palladium:carbon black, 0.103 g), dry Methanol (5.00 mL, 0.123 mol) and Acetic acid (0.300 mL, 0.00528 mol) were combined under nitrogen then purged with hydrogen, heated at 65° 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), 9.13 (s, 1H), 8.21 (d, J=8.6, 2H), 7.78 (s, 2H), 7.42 (t, J=7.9, 1H), 6.32 (s, 1H), 5.99 (s, 1H), 4.71-4.43 (m, 2H), 4.10 (s, 1H), 3.88 (d, J=11.2, 1H), 3.82-3.56 (m, 5H), 3.44 (dd, J=26.9, 16.5, 2H), 2.75 (s, 1H), 2.62 (s, 1H), 2.13 (s, 3H), 1.26 (t, J=5.9, 3H). LC/MS-m/z+461.2 (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-de9ec4eb71484936a25929a8d42b352a
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

Loading…