1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 87461411, compound

HRID 501190Notes

Reaction equation

HRID 501190 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][N:18]([C:21]3[N:26]=[CH:25][C:24]([C:27](O)=[O:28])=[CH:23][N:22]=3)[CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:41][O:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][O:44]1>C(Cl)Cl>[O:44]1[CH2:45][CH2:46][CH2:47][CH2:48][CH:43]1[O:42][NH:41][C:27]([C:24]1[CH:23]=[N:22][C:21]([N:18]2[CH2:17][CH2:16][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:20]=3[CH2:19]2)=[N:26][CH:25]=1)=[O:28]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 68463164HCID 68463164, compound

Product 1

HCID 87461411HCID 87461411, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(9-benzyl-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)pyrimidine-5-carboxylic acid (90 mg) in DCM (5 mL) was added EDCI (74 mg) at 0° C. and the reaction mixture was stirred for 20 min. NH2OTHP (30 mg) was added and the temperature was allowed to attain room temperature. After stirring at room temperature overnight, it was diluted with DCM. The organic layer was washed with water and then concentrated under vacuum. The residue obtained was purified by column chromatography to obtain N-(tetrahydro-2H-pyran-2-yloxy)-2-[9-benzyl-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxamide (60 mg, 53% yield), m/e=484 (M+1).

Workup

  1. customto attain room temperature
  2. stirringAfter stirring at room temperature overnight
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-86b967ceece247d3b7828c70d66a4b3a
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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