4-Methylmorpholine → HCID 70061339, compound

HRID 1741188Notes

Reaction equation

HRID 1741188 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1.CN1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.ClC(OCC(C)C)=[O:28].C[N:35]([C:37]1[CH:42]=CC=CN=1)C>CN(C=O)C>[CH2:24]([O:23][C:22](=[O:28])[CH2:21][CH:37]([NH:35][C:15](=[O:17])[CH2:14][CH2:13][C:12]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[N:3][NH2:2])=[CH:10][CH:9]=1)=[O:18])[CH3:42])[CH3:25]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 62365Isobutyl chloroformateHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 70061339HCID 70061339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[[4-(aminoiminomethyl)phenyl]-amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (5 g, 18 mmol) was added to dry DMF (100 ml) followed by N-methylmorpholine (2.2 g, 22 mmol) and isobutyl chloroformate (2.8 g, 22 mmol) at 25° C. The mixture was stirred for 5 min. Ethyl 3-amino butyrate (2.5 g, 22 mmol) was added followed by dimethylaminopyridine. After 1 hr, the solvent was removed under reduced pressure and the product was purified by reverse phase chromatography (0.05% TPA water/acetonitrile) to give 4.4 g of white solid: 1H NMR (d6 -DMSO) δ 1.06 (d, 3H, J=7 Hz), 2.3-2.6 (m, 6H), 4.05 (m, 3H), 7.8 (s, 4H), 7.9 (d, 1H, J=8 Hz), 9.1 (bs, 2H), 9.2 (bs, 2H), 10.4 (s, 1H); MS (FAB) m/z 349.2 (MH+), 321, 218.

Workup

  1. waitAfter 1 hr
  2. customthe solvent was removed under reduced pressure
  3. customthe product was purified by reverse phase chromatography (0.05% TPA water/acetonitrile)

Sources & evidence

ORD record
ord-8e71e7498b80458987083e4a583fffe4
Source dataset
uspto-grants-1999_10
Patent number
US05973003

Reaction notes

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