Hexane → 2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1H-indol-7-amine

HRID 504792Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:26][CH3:27])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:13][C:12]=3[N+:23]([O-])=O)=[N:6][CH2:5]1.O.NN.C(OCC)(=O)C.CCCCCC>C(O)C.[C].[Pd]>[CH3:27][O:26][CH:3]([O:2][CH3:1])[CH:4]1[S:8][C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:13][C:12]=3[NH2:23])=[N:6][CH2:5]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-[5-(Dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-7-nitro-1H-indole (100 mg) was suspended in ethanol, and 10% palladium-carbon (50% containing water, 50 mg) was added under nitrogen atmosphere. Hydrazine monohydrate (0.07 mL) was added to the mixture, and the mixture was stirred at 90° C. for 2 hr. Hydrazine monohydrate (0.07 mL) was added again, and the mixture was further stirred at 90° C. for 1 hr. The reaction solution was allowed to cool to room temperature, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=30:70-80:20) to give the title compound (27 mg, yield 29%) as a orange oil.

Workup

stirringthe mixture was further stirred at 90° C. for 1 hr
temperatureto cool to room temperature
filtrationthe catalyst was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained crude product

Sources & evidence

ORD record: ord-2bbd00a3a2bc4f6b80270608d5e4aecb
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07777047B2

Reaction notes

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