Diisopropylethylamine → 7-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide

HRID 2364721Notes

Reaction equation

HRID 2364721 reaction equation
[CH2:1]([C@H:3]1[N:12]([CH:13]([CH3:15])[CH3:14])[C:11]2[N:10]=[C:9]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:26](O)=[O:27])=[C:21]4[C:25]=3[O:24][CH2:23][CH2:22]4)[N:8]=[CH:7][C:6]=2[N:5]([CH3:29])[C:4]1=[O:30])[CH3:2].F[B-](F)(F)F.[N:36]1(OC(N(C)C)=[N+](C)C)[C:40]2[CH:41]=[CH:42]C=[CH:44][C:39]=2N=N1.[CH:53]([N:56](C(C)C)CC)(C)C>ClCCl>[CH2:1]([C@H:3]1[N:12]([CH:13]([CH3:15])[CH3:14])[C:11]2[N:10]=[C:9]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:26]([NH:36][CH:40]4[CH2:39][CH2:44][N:56]([CH3:53])[CH2:42][CH2:41]4)=[O:27])=[C:21]4[C:25]=3[O:24][CH2:23][CH2:22]4)[N:8]=[CH:7][C:6]=2[N:5]([CH3:29])[C:4]1=[O:30])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 681080517-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid

Product 1

HCID 681073157-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[(7R)-7-Ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 22f (120 mg, 0.29 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (93 mg, 0.29 mmol) were dissolved in 30 mL of dichloromethane followed by addition of diisopropylethylamine (83 mg, 0.64 mmol) and 1-methyl-piperidyl-4-yl amine (33 mg, 0.29 mmol) successively. The reaction solution was stirred for 3 hours. The resulting solution was washed with saturated sodium carbonate solution (30 mL) and saturated sodium chloride solution (30 mL) successively. The organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-7-ethyl-8-isopropyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 22 (117 mg, yield: 80.0%) as a white solid.

Workup

  1. washThe resulting solution was washed with saturated sodium carbonate solution (30 mL) and saturated sodium chloride solution (30 mL) successively
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddc8bfd60fe3402caaf3261e14f6be97
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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