4-Methylmorpholine → HCID 11638162, compound

HRID 33748Notes

Reaction equation

HRID 33748 reaction equation
C(OC(=O)[N:7]([CH2:12][C:13]1[O:14][CH:15]=[C:16]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)=[O:19])[N:17]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.Cl.Cl.C(N1CCNCC1)(C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH:26]([N:23]1[CH2:24][CH2:25][N:20]([C:18]([C:16]2[N:17]=[C:13]([CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])[O:14][CH:15]=2)=[O:19])[CH2:21][CH2:22]1)([CH3:28])[CH3:27]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122683781-Isopropylpiperazine dihydrochlorideHCID 68623329HCID 68623329, compound

Product 1

HCID 11638162HCID 11638162, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

[4-(4-Isopropyl-piperazine-1-carbonyl)-oxazol-2-ylmethyl]-(2-methoxy-ethyl)-carbamic acid tert-butyl ester. A mixture of the crude material from Step C (1.10 g, 3.67 mmol), 1-isopropyl-piperazine dihydrochloride (0.810 g, 4.03 mmol), 1-hydroxybenzotriazole (0.595 g, 4.40 mmol), and N-methylmorpholine (2.42 mL, 22.0 mmol) in DMF (20 mL) was stirred for 1 h. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.845 g, 4.40 mmol) was added and the mixture was stirred overnight. The reaction mixture was diluted with H2O (500 mL) and extracted with DCM (3×60 mL). The combined organic extracts were washed with H2O (3×300 mL), dried over Na2SO4, filtered and concentrated to yield the crude title compound (1.30 g). MS (ESI): exact mass calcd. for C20H34N4O5, 410.25; m/z found, 411.5 [M+H]+.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with DCM (3×60 mL)
  3. washThe combined organic extracts were washed with H2O (3×300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a88b9ce12cf408893a9a4cb608a439a
Source dataset
uspto-grants-2008_09
Patent number
US07429659B2

Reaction notes

Loading…