Triethylamine → HCID 66802178, compound

HRID 528017Notes

Reaction equation

HRID 528017 reaction equation
Cl[C:2]1[C:11]2[N:10]=[C:9]([O:12][CH3:13])[C:8](=[O:14])[N:7]([CH3:15])[C:6]=2[N:5]=[CH:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][C:19]2([C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:30])[CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)CCC>[CH3:13][O:12][C:9]1[C:8](=[O:14])[N:7]([CH3:15])[C:6]2[N:5]=[CH:4][N:3]=[C:2]([N:16]3[CH2:21][CH2:20][C:19]4([C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][C:22]4=[O:30])[CH2:18][CH2:17]3)[C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18435788Spiro(indole-3,4'-piperidin)-2(1H)-oneHCID 86711708HCID 86711708, compound

Product 1

HCID 66802178HCID 66802178, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100 mL round bottomed flask were placed 4-Chloro-6-methoxy-8-methylpteridin-7(8H)-one (2.00 g, 8.83 mmol, 1 equiv) and spiro[indoline-3,4′-piperidin]-2-one (2.14 g, 10.6 mmol, 1.2 equiv). Anhydrous n-butanol (20 mL) and triethylamine (2.46 mL, 2 equiv) were added and reaction mixture was heated to 80° C. with stirring. The reaction was complete as monitored by LC/MS after 5 hours. The solvent was stripped by rotary evaporation, and the residue rinsed with water (5 mL) to yield a tan precipitate, which was collected by vacuum filtration and rinsed with water to afford the desired product which was used directly without any further purification. 1H NMR (400 MHz, DMSO-d6): δ 10.49 (s, 1H), 8.39 (s, 1H), 7.49 (d, 1H), 7.20 (d, 1H), 6.97 (t, 1H), 6.87 (t, 1H), 4.53-4.45 (m, 4H), 3.80 (s, 3H), 3.55 (s, 3H), 1.93-1.80 (m, 4H). MS (EI) for C20H20N6O3: 393 (MH+).

Workup

  1. customInto a 100 mL round bottomed flask were placed
  2. customreaction mixture
  3. customThe solvent was stripped by rotary evaporation
  4. washthe residue rinsed with water (5 mL)
  5. customto yield a tan precipitate, which
  6. filtrationwas collected by vacuum filtration
  7. washrinsed with water

Sources & evidence

ORD record
ord-f5776642c4dc406b83b86bf1fd8a5de9
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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