Hydrochloric Acid → 3-Fluoro-4-(6-(1-(pyridine-2-yl)cyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde

HRID 1177556Notes

Reaction equation

HRID 1177556 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[CH:21]=[C:20]([C:22]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=5)[CH2:24][CH2:23]4)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:9]([F:31])[CH:8]=1.Cl>C1COCC1>[F:31][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[C:13]1[S:14][C:15]2[CH:21]=[C:20]([C:22]3([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[CH2:24][CH2:23]3)[CH:19]=[CH:18][C:16]=2[N:17]=1)[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671118642-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)-cyclopropyl)benzo[d]thiazole

Product 1

HCID 866387243-Fluoro-4-(6-(1-(pyridine-2-yl)cyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridine-2-yl)cyclopropyl)benzo[d]-thiazole (38 mg, 0.088 mmol) was stirred in THF (1 mL) and 5 N HCl (aq., 0.2 mL) at 50° C. for 2 h. The reaction mixture was cooled to RT, neutralized with satd. NaHCO3, and extracted with EtOAc three times. The organic extracts were dried (MgSO4) and concentrated to give 3-fluoro-4-(6-(1-(pyridine-2-yl)cyclopropyl)benzo[d]thiazol-2-yl)benzaldehyde as a yellow solid. MS (ESI) m/z: Calculated: 374.1; Observed: 375.0 (M++1).

Workup

  1. extractionNaHCO3, and extracted with EtOAc three times
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f24aa9202510466394308859ebd66ed2
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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