Hydrochloric Acid → HCID 86638721, compound

HRID 1177529Notes

Reaction equation

[O:1]1CCCO[CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2([CH:25]4[CH2:29][CH2:28][C:27]([F:31])([F:30])[CH2:26]4)[CH2:24][CH2:23]2)[N:16]=3)=[C:9]([F:32])[CH:8]=1.Cl>C1COCC1>[F:31][C:27]1([F:30])[CH2:28][CH2:29][CH:25]([C:22]2([C:17]3[N:16]=[C:15]4[S:14][C:13]([C:10]5[CH:11]=[CH:12][C:7]([CH:2]=[O:1])=[CH:8][C:9]=5[F:32])=[N:21][C:20]4=[CH:19][CH:18]=3)[CH2:23][CH2:24]2)[CH2:26]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(3,3-difluorocyclopentyl)-cyclopropyl)thiazolo[5,4-b]pyridine was treated with 5 mL THF and 5N HCl was sealed and heated to 70° C. for 1 h. The reaction mixture was cooled, quenched with ice and 10 N NaOH until basic, and diluted with water and DCM. The aq. Layer was extracted with DCM, and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was adsorbed onto 5 g silica gel and dried, purified by silica gel chromatography, 0-40% EA/hexanes, to give (rac)-4-(5-(1-(3,3-difluorocyclopentyl)-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as a solid. MS (ESI) m/z: Calculated: 402.1; Observed: 403.0 (M++1).

Workup

customwas sealed
temperatureThe reaction mixture was cooled
customquenched with ice and 10 N NaOH until basic, and
additiondiluted with water and DCM
extractionThe aq. Layer was extracted with DCM
dry with materialthe combined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a brown oil
customdried
custompurified by silica gel chromatography, 0-40% EA/hexanes

Sources & evidence

ORD record: ord-e6cff623b925407d8ef02be996e18fb5
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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