Ethylmorpholine → HCID 71736383, compound

HRID 919391Notes

Reaction equation

HRID 919391 reaction equation
[CH3:1][C:2]1[C:3]([C:13]2[CH:23]=[CH:22][C:16]([O:17][CH2:18][C:19](O)=[O:20])=[CH:15][CH:14]=2)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O:24]1[CH2:29][CH2:28][CH:27]([CH2:30][NH2:31])[CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(N1CCOCC1)C>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([NH:31][CH2:30][CH:27]3[CH2:28][CH2:29][O:24][CH2:25][CH2:26]3)=[O:20])=[CH:22][CH:23]=2)=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732104-AminomethyltetrahydropyranHCID 89816112HCID 89816112, compound

Product 1

HCID 71736383HCID 71736383, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of product of step 2 (309 mg, 1.00 mmoles) in DMF (3 mL), (tetrahydro-2H-pyran-4-yl)methanamine (126 mg, 1.10 mmoles), HOBT (202 mg, 1.50 mmoles), EDC.HCl (230 mg, 1.20 mmoles) and N-ethyl morpholine (345 mg, 3.00 mmoles) were added and reaction mixture was stirred at room temperature for 20 hours under nitrogen atmosphere. The reaction mixture was poured into ice cold water, solid separated was filtered, washed with water and dried over P2O5 under vacuum to yield 260 mg of title product as pale yellow solid.

Workup

  1. customreaction mixture
  2. additionThe reaction mixture was poured into ice cold water, solid
  3. customseparated
  4. filtrationwas filtered
  5. washwashed with water
  6. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-4ef5c3c93d5a4df98640577d064fed13
Source dataset
uspto-grants-2016_03
Patent number
US09273041B2

Reaction notes

Loading…