Dimethylformamide → HCID 70061687, compound

HRID 1941561Notes

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.CN1CC[O:23][CH2:22]C1.ClC(OCC(C)C)=O.NCO[C:37]1[C:38](=[O:47])[O:39][C:40]2[C:45]([CH:46]=1)=C[CH:43]=[CH:42][CH:41]=2.C[N:49](C1C=CC=CN=1)C.CN([CH:60]=[O:61])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:49][CH:46]([C:45]2[CH:40]=[CH:41][C:42]([O:23][CH3:22])=[CH:43][C:60]=2[OH:61])[CH2:37][C:38]([OH:39])=[O:47])=[O:17])=[CH:9][CH:10]=1

Participants

Reactant 6

HCID 6228Dimethylformamide

HCID 79724-Methylmorpholine

HCID 218852-Dimethylaminopyridine

HCID 62365Isobutyl chloroformate

HCID 57235227HCID 57235227, compound

HCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 70061687HCID 70061687, compound

Procedure

4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (4.6 g, 17 mmol) was added to dry DMF (225 ml) followed by N-methylmorpholine (1.2 g, 17 mmol) and isobutyl chloroformate (2.3 g, 17 mmol) at 25° C. The mixture was stirred for 5 min. Amino methoxy coumarin (3.0 g, 17 mmol) 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 3.5 g of a white solid: 1H NMR (d6 -DMSO) δ2.37 (t, 2H, J=7.3 Hz), 2.55 (m, 2H), 2.57 (t, 2H, J=7.1 Hz), 3.57 (s, 6H), 4.35 (m, 1H), 7.79 (s, 4H), 7.99 (d, 1H,J=8.1 Hz), 9.1 (bs, 2H), 9.19 (bs, 2H), 10.42 (s, 1H); MS (FAB) m/z 393.2 (MH+).

Workup

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

Sources & evidence

ORD record: ord-11a71a470abb49419b5dec5efdf080b1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05703125

Reaction notes

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