Water → HCID 86638728, compound

HRID 1177630Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:22][CH2:21]1)[N:14]=2)[C:5](O)=[O:6].O.[N-:30]=[N+:31]=[N-:32].[Na+]>S(Cl)(Cl)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[S:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[C:15]([C:20]1([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:21][CH2:22]1)[N:14]=2)[C:5]([N:30]=[N+:31]=[N-:32])=[O:6]

Participants

Conditions

Temperature: 65 °C

Procedure

3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoic acid (105 mg, 269 μmol) was dissolved in thionyl chloride (5 mL) and was stirred at 65° C. for 1 h. The reaction mixture was concentrated before it was dissolved in DCM (3 mL); to this was added tetrabutylammonium bromide (8 mg, 27 μmol), water (269 μl, 269 μmol), and sodium azide (21.0 mg, 323 μmol) at 0° C. before it was stirred for 2 h. The reaction mixture was diluted with 75 mL of DCM, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, separated, dried over sodium sulfate, and concentrated via rotovap to give 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzoyl azide. MS (ESI) m/z: Calculated: 415.1; Observed: 416.0 (M++1).

Workup

concentrationThe reaction mixture was concentrated before it
dissolutionwas dissolved in DCM (3 mL)
stirringwas stirred for 2 h
additionadded to a separatory funnel
custompartitioned with water
washwashed 2 times with 50 mL of water
customseparated
dry with materialdried over sodium sulfate
concentrationconcentrated via rotovap

Sources & evidence

ORD record: ord-e84ae3fb29df40feadadc777bea6120a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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