HCID 67412568, compound → HCID 67412650, compound

HRID 2035523Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)=[CH:10][C:11]=1[NH:12][CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=1)=[O:5])C>CO.[OH-].[Na+].O>[F:20][C:18]1[CH:19]=[C:14]([CH:15]=[C:16]([F:21])[CH:17]=1)[CH2:13][NH:12][C:11]1[CH:10]=[C:9]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:27][CH:28]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

2.99 g of 4-[(3,5-difluorobenzyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxylic acid ethyl ester was dissolved in 30 mL of methanol, to which 12 mL of 4 mol/L sodium hydroxide in water was added at room temperature, and stirred at 80° C. for 1.5 hour. After cooling, methanol was evaporated, weakly acidified (about pH 4) by adding 6 mol/L hydrochloric acid in water under ice cooling, the deposited crystals were filtered, and washed with water and methanol. After air-drying, they were dried under reduced pressure (60-70° C., for 3 hours) to obtain 2.72 g (yield 97%) of 4-[(3,5-difluorobenzyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxylic acid as a light reddish purple crystalline powder.

Workup

additionwas added at room temperature
temperatureAfter cooling
custommethanol was evaporated
additionby adding 6 mol/L hydrochloric acid in water under ice cooling
filtrationthe deposited crystals were filtered
washwashed with water and methanol
customAfter air-drying
customthey were dried under reduced pressure (60-70° C., for 3 hours)

Sources & evidence

ORD record: ord-ad86e39caeaf48a2ab1081915a72642e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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