Hydrochloric Acid → HCID 117778806, compound

HRID 2206576Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]([N:6]1[C:10]2[N:11]=[CH:12][S:13][C:9]=2[C:8]([C:14]#N)=[C:7]1[CH3:16])[CH3:5].[OH-:17].[Na+].Cl.O1CCCC1.C[OH:26]>O>[CH3:1][O:2][CH2:3][CH:4]([N:6]1[C:10]2[N:11]=[CH:12][S:13][C:9]=2[C:8]([C:14]([OH:26])=[O:17])=[C:7]1[CH3:16])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(1-methoxypropan-2-yl)-5-methyl-4H-pyrrolo[2,3-d]thiazole-6-carbonitrile (1.0 g, 4.25 mmol) in tetrahydrofuran/methanol=1:1 (30 mL) was added sodium hydroxide (680 mg, 17 mmol) resolved in 15 mL water. The resulting reaction system was heated to 80° C. and allowed to stir for 24 hours at 80° C. The pH was adjusted to around 7 by progressively adding 4N hydrogen chloride below 0° C., solvent and water was removed in reduced pressure to give the title compound (500 mg, 46%) as an yellow solid. LCMS (M+H+) m/z: calc'd. 254.07. found 254.7.

Workup

customThe resulting reaction system
customwas removed in reduced pressure

Sources & evidence

ORD record: ord-d831bb3985174aa6b9711a87cea31721
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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