Hydrochloric Acid → HCID 90052301, compound

HRID 2284753Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 4-((5-(5-(1,3-dioxoisoindolin-2-yl)-1-pentyn-1-yl)-4-(methyl(propyl)amino)pyrimidin-2-yl)amino)benzoate (H7, 634 mg) in tetrahydrofuran (6.2 mL), 2.0 mol/L aqueous sodium hydroxide (3.1 mL) was added at room temperature, and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled to room temperature, and then 1.0 mol/L aqueous hydrochloric acid was added to the reaction mixture until the mixture became acidic. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain 2-((5-(2-((4-carboxyphenyl)amino)-4-(methyl(propyl)amino)pyrimidin-5-yl)-4-pentyn-1-yl)carbamoyl)benzoic acid (H8, 526 mg) as white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid matter was taken by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-b50c00390bcc4d05893e2032a5b02384
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

Loading…