Thionyl Chloride → HCID 67111742, compound

HRID 1177595Notes

Reaction equation

[F:1][C:2]1([F:9])[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.S(Cl)(Cl)=O.[O:14]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]3[C:33]([N:34]=2)=[CH:32][CH:31]=[C:30]([Sn](C)(C)C)[N:29]=3)=[C:22]([F:39])[CH:21]=1>C1(C)C=CC=CC=1>[O:16]1[CH2:17][CH2:18][CH2:19][O:14][CH:15]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]3[C:33]([N:34]=2)=[CH:32][CH:31]=[C:30]([C:6]([CH:4]2[CH2:3][C:2]([F:1])([F:9])[CH2:5]2)=[O:8])[N:29]=3)=[C:22]([F:39])[CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3,3-difluorocyclobutanecarboxylic acid (542.6 mg, 3.99 mmol) in thionyl chloride (5.24 mL, 71.8 mmol) was heated at 70° C. for 1 h and then concentrated in vacuo. 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)thiazolo[5,4-b]pyridine (1.08 g, 2.254 mmol) was added to the residue, and the mixture was taken up in toluene (20.0 mL) and stirred under argon at 80° C. for 16 h. The reaction mixture was then concentrated onto silica gel and chromatographically purified (0-60% EtOAc/hexanes) to provide (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)thiazolo[5,4-b]pyridin-5-yl)(3,3-difluorocyclobutyl)methanone as an off-white solid. MS (ESI) m/z: Calculated: 434.1; Observed: 435.0 (M++1).

Workup

concentrationconcentrated in vacuo
concentrationThe reaction mixture was then concentrated onto silica gel
customchromatographically purified (0-60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e58a0723120f49d6b2619bd7de7114c2
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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