Piperidin-4-ol → 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-6-(4-hydroxypiperidine-1-carbonyl)-2-morpholino-4H-chromen-4-one

HRID 41181Notes

Reaction equation

HRID 41181 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[CH:15]=[C:16]([C:31](O)=[O:32])[CH:17]=[C:18]3[C:23]=2[O:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:19]3=[O:30])[CH:5]=[C:6]([F:8])[CH:7]=1.[NH:34]1[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]1>>[F:8][C:6]1[CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[CH:15]=[C:16]([C:31]([N:34]3[CH2:39][CH2:38][CH:37]([OH:40])[CH2:36][CH2:35]3)=[O:32])[CH:17]=[C:18]3[C:23]=2[O:22][C:21]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[CH:20][C:19]3=[O:30])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 866724028-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 866724088-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-6-(4-hydroxypiperidine-1-carbonyl)-2-morpholino-4H-chromen-4-oneYield 66.2%

Procedure

Title compound was prepared using an analogous procedure to that described in Example 1.01. 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (105 mg, 0.21 mmol) was reacted with piperidin-4-ol (22.48 mg, 0.22 mmol) to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-6-(4-hydroxypiperidine-1-carbonyl)-2-morpholino-4H-chromen-4-one (75 mg, 66%) as a white solid.

Workup

  1. customTitle compound was prepared

Sources & evidence

ORD record
ord-4c67374c9990495d9b721c7b8e4d7cfd
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

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