Dimethylformamide → HCID 86751794, compound

HRID 1941551Notes

Reaction equation

HRID 1941551 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]C1.Cl[C:27]([O:29][CH2:30]C(C)C)=[O:28].CN(C1C=CC=[CH:39][N:38]=1)C.CN(C=[O:47])C>>[NH2:2][N:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([NH:38][CH2:39][CH:25]([C:24]([O:23][CH3:22])=[O:47])[C:27]([O:29][CH3:30])=[O:28])=[O:17])=[CH:9][CH:10]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 62365Isobutyl chloroformateHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 86751794HCID 86751794, compound

Procedure

4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (5.0 g, 18.5 mmol) was added to dry DMF (250 ml) followed by N-methylmorpholine (1.7 g, 18.5 mmol) and isobutyl chloroformate (2.8 g, 17 mmol) at 25° C. The mixture was stirred for 5 min. Dimethy12-(aminomethyl)malonate (from Step 1; 1 eq) was added followed by dimethylaminopyridine. After 1 h, the solvent was removed under reduced pressure and the product purified by reverse phase chromatography (water/acetonitrile) to result in 2.0 g of a white solid: 1H NMR (d6 -DMSO) δ2.57 (m, 2H), 2.67 (m, 2H), 3.47 (m, 2H), 3.5 (s, 6H), 3.51 (m, 1H), 7.79 (s, 4H), 8.1 (t, 1H, J=7 Hz), 8.7 (bs, 2H), 9.09 (bs, 2H), 10.32 (s, 1H); MS (FAB) m/z 379.0 (MH+).

Workup

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

Sources & evidence

ORD record
ord-1af86b03d6cc42e3b33acc84f2012402
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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