Hydrochloric Acid → 5-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

HRID 2060634Notes

Reaction equation

[OH:1][CH2:2][CH:3]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[N:19][C:18]=2[C:34]([O:36]CC)=[O:35])[CH:13]=[CH:12][CH:11]=1)[N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.CO.[OH-].[K+].Cl>C(O)(C)(C)C>[OH:1][CH2:2][CH:3]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[N:19][C:18]=2[C:34]([OH:36])=[O:35])[CH:13]=[CH:12][CH:11]=1)[N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 5-{[6-(2-hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate (68 mg, 0.126 mmol) was taken up in tert-butanol (1.3 mL) and methanol (1.3 mL) and aqueous 1.0 M potassium hydroxide (0.63 mL, 0.63 mmol) was added. The resulting slurry was stirred at 60° C. for 4.5 hrs (the slurry became a homogenous yellow solution soon after reaching 60° C.). The reaction was cooled to room temperature and neutralized with 0.63 mL 1M aqueous hydrochloric acid. A yellow precipitate then formed. The resulting slurry was concentrated under reduced pressure, suspended in methanol, and concentrated again to afford the title compound as a yellow solid. LRMS (APCI) calcd for C24H29N6O5S [M+H]+, 513.2; found 513.0.

Workup

customafter reaching 60° C.
customA yellow precipitate then formed
concentrationThe resulting slurry was concentrated under reduced pressure
concentrationconcentrated again

Sources & evidence

ORD record: ord-f6a88a565b2848299562e3dbdc6ba634
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278335B2

Reaction notes

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