Diisopropylethylamine → HCID 53353524, compound

HRID 451433Notes

Reaction equation

HRID 451433 reaction equation
Cl.[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:23][C:24]1[N:28]=[C:27](Cl)[S:26][N:25]=1.C(N(CC)C(C)C)(C)C>O1CCCC1.O>[CH2:2]([C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:27]3[S:26][N:25]=[C:24]([Br:23])[N:28]=3)[CH2:19][CH2:18]2)[N:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 67344140(4-Benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride

Product 1

HCID 53353524HCID 53353524, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride (125 mg, 0.39 mmol), 3-bromo-5-chloro-[1,2,4]thiadiazol (39 mg, 0.19 mmol) and N,N-diisopropylethyl amine (66 L, 0.39 mmol) in tetrahydrofurane (3 mL) was heated to 95° C. 4.5 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent. The title compound was obtained as a colorless oil (84 mg, 96%).

Workup

  1. custom4.5 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using a gradient from CH2Cl2 to CH2Cl2/MeOH 19:1 (v/v) as eluent

Sources & evidence

ORD record
ord-1dc31b0d98854a9eb3ed1481c3cfe4d5
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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