5,6-diethoxy-7-fluoro-3H-isoindol-1-ylamine → Atopaxar Hydrobromide

HRID 244337Notes

Reaction equation

[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]([O:17][CH3:18])=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=1)=[O:4].[CH2:23]([O:25][C:26]1[CH:27]=[C:28]2[C:32](=[C:33]([F:38])[C:34]=1[O:35][CH2:36][CH3:37])[C:31]([NH2:39])=[N:30][CH2:29]2)[CH3:24]>O1CCCC1>[BrH:1].[C:19]([C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:30]2[CH2:29][C:28]3[C:32](=[C:33]([F:38])[C:34]([O:35][CH2:36][CH3:37])=[C:26]([O:25][CH2:23][CH3:24])[CH:27]=3)[C:31]2=[NH:39])[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]=1[O:17][CH3:18])([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 6 °C

Procedure

2-Bromo-1-(3-tert-butyl-4-methoxy-5-morpholinophenyl)ethanone (550 g, 1.485 mol) was dissolved in tetrahydrofuran (3 L) and subjected to clarifying filtration. A solution of 5,6-diethoxy-7-fluoro-3H-isoindol-1-ylamine (300 g, 1.254 mol) in tetrahydrofuran (4.5 L) was added dropwise to the above solution in 3 portions (100 g/1.5 L×3 times) while stirring at the ambient temperature of 6° C. After completion of the dripping, crystals were deposited. After stirring for 18 hours, the deposited crystals were collected by filtration and washed with ice-cooled tetrahydrofuran (1.2 L) to give 696.5 g of the captioned compound as wet crystals.

Workup

filtrationfiltration
stirringAfter stirring for 18 hours
filtrationthe deposited crystals were collected by filtration
washwashed with ice-
temperaturecooled tetrahydrofuran (1.2 L)

Sources & evidence

ORD record: ord-0138e8aecc9c440480d48ab2cca167c8
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658620B2

Reaction notes

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