Water → Methyl 4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-2,3-dihydro-1H-indene-2-carboxylate

HRID 877176Notes

Reaction equation

HRID 877176 reaction equation
[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7](Cl)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[NH2:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1[CH2:40][CH:41]([C:47]([O:49][CH3:50])=[O:48])[CH2:42]2.O>ClCCl>[CH:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:22](=[O:23])[CH2:21][O:20][C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:18]3)=[CH:12][CH:11]=2)[C:7]([NH:37][C:38]2[CH:46]=[CH:45][CH:44]=[C:43]3[C:39]=2[CH2:40][CH:41]([C:47]([O:49][CH3:50])=[O:48])[CH2:42]3)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 53350286Methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylateHCID 58136651HCID 58136651, compound

Product 1

HCID 58136482Methyl 4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-2,3-dihydro-1H-indene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

337 mg (0.821 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl chloride (enantiomer 1; Example 81A) were dissolved in 8 ml of dichloromethane, and 83 mg (0.821 mmol) of triethylamine were added. 157 mg (0.821 mmol) of methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylate (enantiomer 1; Example 89A), dissolved in 2 ml of dichloromethane, were added to the mixture. The mixture was stirred at room temperature overnight. Water was then added, and the reaction solution was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1→1:1). This gave 182 mg (0.32 mmol, 39% of theory) of the title compound.

Workup

  1. additionwere added to the mixture
  2. extractionthe reaction solution was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1→1:1)

Sources & evidence

ORD record
ord-82a9e295aa884dc4b53bd32255acd5ea
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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