Potassium Sodium Tartrate → HCID 21916253, compound

HRID 1246314Notes

Reaction equation

HRID 1246314 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH3:8])[CH2:3][CH2:2]1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:22]2[CH:23]=[C:24](Cl)[N:25]([C:26]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=3[CH3:34])[C:21]2=[N:20][C:19]=1[CH3:36])=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=[O:40].[Na+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]([CH2:6][CH2:7][CH3:8])[C:16]([C:18]2[N:22]3[CH2:23][C:24](=[O:40])[N:25]([C:26]4[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])[C:21]3=[N:20][C:19]=2[CH3:36])=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 117787Cyclopropanemethanamine, N-propyl-HCID 16682925TrimethylaluminumHCID 20780222HCID 20780222, compound

Product 1

HCID 21916253HCID 21916253, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of N-cyclopropylmethylpropylamine (0.22 mL, 1.530 mmol) in toluene (1.5 mL) at 0° C. was added 2.0M solution of trimethylaluminum in toluene (0.77 mL, 1.530 mmol). The clear solution was warmed to room temperature and stirred for 1 h. A solution of 6-chloro-2-methyl-7-(2,4,6-trimethyl-phenyl)-7H-imidazo[1,2-a]imidazole-3-carboxylic acid ethyl ester (20.0 mg, 0.058 mmol) in toluene (1.5 mL) was added at 0° C. via cannula. The reaction mixture was heated at 80° C. for 2 h. A solution of Rochelle's salt (2.0 mL) was added carefully at 0° C. and the mixture was vigorously stirred for 30 min. The crude product was extracted with ethyl acetate. The combined organic extracts were dried with MgSO4. The solvent was removed under reduced pressure and the crude product was purified by a reverse-phase preparative HPLC. Yield—3.6 mg (12%). 1H NMR (CD3CN, 500 MHz) δ 7.07 (s, 2H), 4.73 (s, 2H), 3.57 (t, J=7.1 Hz, 2H), 3.37 (d, J=6.9 Hz, 2H), 2.35 (s, 3H), 2.19 (s, 3H), 2.14 (s, 6H), 1.65 (sextet, J=7.3 Hz, 2H), 1.08 (m, 1H), 0.90 (t, J=7.4 Hz, 3H), 0.56 (m, 2H), 0.21 (m, 2H); LC/MS: tR=1.67 min., MS: [M+H]=395.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 2 h
  2. stirringthe mixture was vigorously stirred for 30 min
  3. extractionThe crude product was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by a reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-dbb2279618714a44a9c7b14d7a9c22c5
Source dataset
uspto-grants-2006_10
Patent number
US07125990B2

Reaction notes

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