Cesium carbonate → HCID 23092675, compound

HRID 2235355Notes

Reaction equation

HRID 2235355 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[CH:6][C:7]([N+:15]([O-:17])=[O:16])=[C:8]([NH:11]C(=O)C)[CH:9]=2)[NH:4][C:3]1=[O:18].Cl.Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+]>Cl>[NH2:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16])[N:4]([CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[C:3](=[O:18])[C:2]2([CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 122962834-(3-Chloropropyl)morpholinium chlorideHCID 23092658N-(3,3-Dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)acetamide

Product 1

HCID 23092675HCID 23092675, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (0.5 g) is alkylated using 4-(3-chloro-propyl)-morpholine hydrocloride (0.57 g; 2.85 mmol), Cs2CO3 (1.55 g; 4.75 mmol) and a catalytic amount of nBU4NI at 70° C. for 4 days. After aqueous work-up the crude material is de-acetylated in hydrochloric acid (6 N, 20 ml) at 80° C. in 4 h. After aqueous work-up 5-amino-3,3-dimethyl-1-(3-morpholin-4-yl-propyl)-6-nitro-1,3-dihydro-indol-2-one (0.67 g) is obtained.

Sources & evidence

ORD record
ord-3b57adae5bcf4ae29b4c363769367ece
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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