Morpholine → HCID 59525697, compound

HRID 385845Notes

Reaction equation

HRID 385845 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:4][CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][CH2:10][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59526147HCID 59526147, compound

Product 1

HCID 59525697HCID 59525697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(6-bromopyridin-2-yl)methoxy]acetic acid (1.6 g, 7.5 mmol) and morpholine (0.65 g, 7.5 mmol) in dichloromethane at 0° C. was added N-ethyl-N-isopropylpropan-2-amine (3.9 mL, 22.5 mmol), 1-hydroxybenzotriazole hydrate (1.5 g, 11.25 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.1 g, 11.25 mmol). The reaction mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography, eluting with ethyl acetate:hexanes (3:7) to afford the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography
  3. washeluting with ethyl acetate:hexanes (3:7)

Sources & evidence

ORD record
ord-53ddbcbc9fa44a0187090a080a71e43a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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