Tetrahydrofuran → HCID 57785922, compound

HRID 1399340Notes

Reaction equation

HRID 1399340 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18](Cl)=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([OH:26])[CH2:24][CH3:25])=[CH:4][CH:3]=1.[CH:27]1([C:30]([OH:32])=O)[CH2:29][CH2:28]1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].[O:54]1CCC[CH2:55]1>CN(C)C1C=CN=CC=1>[CH:27]1([C:30]([O:26][CH:23]([C:5]2[C:6]3[N:7]4[CH2:14][CH2:13][CH2:12][N:11]([C:15]5[CH:20]=[CH:19][C:18]([O:54][CH3:55])=[CH:17][C:16]=5[Cl:22])[C:8]4=[N:9][C:10]=3[C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:24][CH3:25])=[O:32])[CH2:29][CH2:28]1

Participants

8

Reactant 6

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44156374HCID 44156374, compound

Product 1

HCID 57785922HCID 57785922, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (50 mg, 0.123 mmol), cyclopropanecarboxylic acid (16 mg, 0.185 mmol), triethylamine (0.018 mL, 0.246 mmol) and 4-dimethylaminopyridine (23 mg, 0.185 mmol) in tetrahydrofuran (2 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (47 mg, 0.185 mmol) at room temperature. The mixture was stirred at room temperature for 18 hr. Saturated aqueous ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 20-70% ethyl acetate/n-hexane gradient mixture and recrystallization from 2-propanol/n-hexane to give the title compound (25 mg, 0.0527 mmol, 43%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with a 20-70% ethyl acetate/n-hexane gradient mixture and recrystallization from 2-propanol/n-hexane

Sources & evidence

ORD record
ord-5a60de0ec34d4a9685f9464391342e83
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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