Triethylamine → HCID 66799879, compound

HRID 528015Notes

Reaction equation

HRID 528015 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][CH:19]([N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][C:23]2=[O:31])[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[CH2:17][CH2:18][CH:19]([N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[NH:24][C:23]4=[O:31])[CH2:20][CH2:21]3)[C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 86711708HCID 86711708, compound

Product 1

HCID 66799879HCID 66799879, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-6-methoxy-8-methylpteridin-7(8H)-one (4.00 g, 17.7 mmol, 1 equiv) and 1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (3.83 g, 17.7 mmol, 1 equiv) were suspended in anhydrous n-butanol (40 mL) in a 250 mL one-necked round-bottomed flask. Triethylamine (35.30 mmol, 3.57 g, 4.92 mL, 2 equiv) was added to the flask, and the stirred reaction mixture was heated to 80° C. The reaction was monitored by LC/MS and was complete after 6 hours. The resulting tan colored suspension was cooled to room temperature and filtered. The collected solid was washed with n-butanol (10 mL) and anhydrous ether (25 mL). The solid was air-dried to give the desired material, 6-methoxy-8-methyl-4-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]pteridin-7(8H)-one as a pale yellow colored solid (5.69 g, 79% yield.). 1H NMR (400 MHz, DMSO-d6): δ 10.83 (broad s, 1H), 8.33 (s, 1H), 7.13 (m, 1H), 6.93 (m, 3H), 5.30 (d, 1H), 4.54 (1H), 3.88 (s, 3H), 3.55 (s, 3H), 3.20 (t, 2H), 2.42 (dq, 2H), 1.82 (d, 2H). MS (EI) for C20H21N7O3: 408 (MH+).

Workup

  1. customthe stirred reaction mixture
  2. temperatureThe resulting tan colored suspension was cooled to room temperature
  3. filtrationfiltered
  4. washThe collected solid was washed with n-butanol (10 mL) and anhydrous ether (25 mL)
  5. customThe solid was air-dried

Sources & evidence

ORD record
ord-cb2523ee6a9a4d7e88aa8f575e1a93ac
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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