Dimethylformamide → 3,4-dimethoxy-N-[3-(2-morpholin-4-yl-indan-5-ylcarbamoyl)-benzyl]-benzamide

HRID 418362Notes

Reaction equation

HRID 418362 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7].[N:24]1([CH:30]2[CH2:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([NH2:39])[CH:36]=3)[CH2:31]2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CN(C=O)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:12]([C:13](=[O:15])[NH:39][C:35]2[CH:36]=[C:37]3[C:32](=[CH:33][CH:34]=2)[CH2:31][CH:30]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH2:38]3)[CH:11]=1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 448195433-[(3,4-Dimethoxy-benzoylamino)-methyl]-benzoic acidHCID 591908752-Morpholin-4-yl-indan-5-ylamine

Product 1

HCID 591908293,4-dimethoxy-N-[3-(2-morpholin-4-yl-indan-5-ylcarbamoyl)-benzyl]-benzamideYield 62.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the 3-[(3,4-dimethoxy-benzoylamino)-methyl]-benzoic acid (100 mg, 0.32 mmol) and 2-morpholin-4-yl-indan-5-ylamine (84 mg, 0.38 mmol) 1.5 mL of DMF. To this was added TBTU (122 mg, 0.38 mmol), and the vial warmed until a clear solution was obtained. The solution was stirred at room temperature. Stirring continued for 20 h total. Diluted with EtOAc and washed with Na2CO3, water and brine. The organic layer was dried over MgSO4, evaporated and purified by column chromatography, CH2Cl2/MeOH gradient 1-10%, to give 103 mg of 3,4-dimethoxy-N-[3-(2-morpholin-4-yl-indan-5-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray, 516, (M+H).

Workup

  1. temperaturethe vial warmed until a clear solution
  2. customwas obtained
  3. stirringStirring
  4. washwashed with Na2CO3, water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. custompurified by column chromatography, CH2Cl2/MeOH gradient 1-10%

Sources & evidence

ORD record
ord-38fc7e2cdf364ba882f1ffe4770a58cf
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

Loading…