Dimethylformamide → (E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid (5-morpholin-4-yl-indan-1-yl)amide

HRID 1446554Notes

Reaction equation

HRID 1446554 reaction equation
CN(C=O)C.FC(F)(F)C(O)=O.[Cl:13][CH2:14][CH2:15][CH2:16]/[C:17](=[CH:21]\[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[C:24]([O:34][CH3:35])[CH:23]=1)/[C:18]([OH:20])=O.[N:36]1([C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][CH:50]=2)[CH:47]([NH2:51])[CH2:46][CH2:45]3)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C1C=CC2N(O)N=NC=2C=1>C(N(C(C)C)CC)(C)C.C(Cl)CCl>[N:36]1([C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][CH:50]=2)[CH:47]([NH:51][C:18](=[O:20])/[C:17](=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:24]([O:34][CH3:35])[CH:23]=2)/[CH2:16][CH2:15][CH2:14][Cl:13])[CH2:46][CH2:45]3)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 669617445-Morpholin-4-yl-indan-1-ylamine

Product 1

HCID 66960274(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid (5-morpholin-4-yl-indan-1-yl)amideYield 78.3%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a DMF (5.0 mL) solution of (E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetic acid salt (3.0 g) obtained in Example 418 and 5-morpholin-4-yl-indan-1-ylamine (1.80 g), IPEA (5.18 mg), EDC (3.84 g) and HOBT (2.71 g) were added one by one, and the reaction solution was agitated at room temperature for 1 hour. After confirming disappearance of the starting materials, the solvent was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the organic layer was partitioned. After washed with a saturated saline solution the organic layer, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 2.80 g of the title compound was obtained by purifying the obtained residue by silica gel chromatography (elution solvent:heptane-ethyl acetate system). The physical properties of the compound are as follows.

Workup

  1. concentrationthe solvent was concentrated under reduced pressure, water and ethyl acetate
  2. additionwere added to the residue
  3. customthe organic layer was partitioned
  4. washAfter washed with a saturated saline solution the organic layer, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cd59e13ab234d0f9a16c73d56ea2e32
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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