Hydrochloric Acid → 4-({[4-(Pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid

HRID 252809Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[N:8]=2)[CH:2]=1.O[Li].O.Cl>C1COCC1.CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=3)[N:8]=2)[CH:2]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a stirred solution of 41 (3.68 g, 11.5 mmol) in a mixture of THF (23 ml) and MeOH (23 ml) was added a solution of LiOH—H2O (1.06 g, 25.3 mmol) in water (11.5 ml) at room temperature. The reaction mixture was stirred at 40° C. overnight, cooled to the room temperature, and an aqueous solution of HCl (12.8 ml, 2N) was added (pH˜4-5). The mixture was concentrated to dryness; the formed solid was triturated with water, filtered off, washed with minimum H2O and dried to afford the title compound 42 (3.44 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.83 (bs, 1H), 9.23 (bs, 1H), 8.73-8.66 (m, 1H) 8.46-8.36 [m, included at 8.42 (d, J=5.1 Hz), 2H], 8.02 (t, J=6.3 Hz, 1H), 7.91 (d, J=8.2 Hz, 2H), 7.60-7.40 (m, 3H), 7.28 (d, J=5.1 Hz, 1H), 4.67 (d, J=6.3 Hz, 2H).

Workup

temperaturecooled to the room temperature
concentrationThe mixture was concentrated to dryness
customthe formed solid was triturated with water
filtrationfiltered off
washwashed with minimum H2O
customdried

Sources & evidence

ORD record: ord-2884f6eb6f9a48c59b301d27df185e1e
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868205B2

Reaction notes

Loading…