Triethylamine → HCID 68005911, compound

HRID 1914617Notes

Reaction equation

HRID 1914617 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[C:14]([C:17](O)=[O:18])[N:15]([CH3:16])[C:9]=2[N:8]=[C:7]1[CH3:26].Cl.[NH2:31][CH:32]1[CH2:37][CH2:36][N:35]([C:38](=[O:41])[CH2:39][OH:40])[CH2:34][CH2:33]1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])=[C:14]([C:17]([NH:31][CH:32]3[CH2:33][CH2:34][N:35]([C:38](=[O:41])[CH2:39][OH:40])[CH2:36][CH2:37]3)=[O:18])[N:15]([CH3:16])[C:9]=2[N:8]=[C:7]1[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66893119HCID 66893119, compoundHCID 68005510HCID 68005510, compound

Product 1

HCID 68005911HCID 68005911, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the compound of Reference Example 47 (84 mg, 0.19 mmol), 1N aqueous sodium hydroxide solution (2 mL), THF (2 mL) and ethanol (2 mL) was stirred at 60° C. for 3 hr. The reaction mixture was neutralized with 2N hydrochloric acid (1 mL), and concentrated under reduced pressure, and the precipitate was filtered and washed with water to give 3-(3-fluorobenzyl)-2,7-dimethyl-4-oxo-5-(2,2,2-trifluoroethoxy)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a powder (59 mg, 75%). A mixture of 3-(3-fluorobenzyl)-2,7-dimethyl-4-oxo-5-(2,2,2-trifluoroethoxy)-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (59 mg, 0.14 mmol), 2-(4-aminopiperidin-1-yl)-2-oxoethanol hydrochloride (35 mg, 0.18 mmol), HOBt (28 mg, 0.18 mmol), WSCD (35 mg, 0.18 mmol) and triethylamine (18 mg, 0.18 mmol) in DMF (5 mL) was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by aminosilica gel column chromatography (eluate, hexane:ethyl acetate=1:1→0:100), and recrystallized from ethyl acetate-hexane to give the title compound (13 mg, 17%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by aminosilica gel column chromatography (eluate, hexane:ethyl acetate=1:1→0:100)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e48c92fc80a2405491932ea217261898
Source dataset
uspto-grants-2013_12
Patent number
US08614208B2

Reaction notes

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