1-[5-Methoxy-2-nitro-4-[3-(1-pyrrolidinyl)propoxy]phenyl]cyclobutanecarbonitrile → HCID 76332101, compound

HRID 925128Notes

Reaction equation

HRID 925128 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]([CH3:22])([CH3:21])[C:19]#[N:20])=[C:12]([N+:23]([O-])=O)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C(OCCCN2CCCC2)=CC([N+]([O-])=O)=C(C2(C#N)CCC2)C=1>>[CH:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:13]([C:18]([CH3:22])([CH3:21])[C:19]([NH2:20])=[N:23]3)=[CH:14][C:15]=2[O:16][CH3:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 1183893681-[5-Methoxy-2-nitro-4-[3-(1-pyrrolidinyl)propoxy]phenyl]cyclobutanecarbonitrileHCID 118389370HCID 118389370, compound

Product 1

HCID 76332101HCID 76332101, compoundYield 37.2%

Procedure

2-(4-(3-cyclopentylpropoxy)-5-methoxy-2-nitrophenyl)-2-methylpropanenitrile (0.126 g, 0.365 mmol), from Step 3, was treated in a manner analogous to that described for 1-(5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)phenyl)cyclobutanecarbonitrile in Step 5 of Example 7. Purification of the crude product by flash chromatography (silica gel, 10-30% MeOH/DCM) afforded 43 mg (37%) of 6-(3-cyclopentylpropoxy)-5-methoxy-3,3-dimethyl-3H-indol-2-amine 1H NMR (400 MHz, DMSO) δ 7.20 (s, 1H), 6.80 (s, 1H), 3.93 (t, J=6.5 Hz, 2H), 3.75 (s, 3H), 1.84-1.67 (m, 6H), 1.62-1.54 (m, 2H), 1.53-1.48 (m, 2H), 1.48-1.44 (m, 5H), 1.43-1.40 (m, 2H), 1.14-1.02 (m, 2H). MS (ESI) m/z 317 (M+H)+.

Workup

  1. customPurification of the crude product by flash chromatography (silica gel, 10-30% MeOH/DCM)

Sources & evidence

ORD record
ord-88eb95cb997d4c6894d565df704214a5
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

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