Ammonium Chloride → (2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone

HRID 1177553Notes

Reaction equation

HRID 1177553 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Mg]Cl.[O:9]1[CH2:14][CH2:13][CH2:12][O:11][CH:10]1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][C:23]3[CH:29]=[C:28]([C:30](N(OC)C)=[O:31])[CH:27]=[CH:26][C:24]=3[N:25]=2)=[C:17]([F:36])[CH:16]=1.[NH4+].[Cl-]>C1COCC1>[O:11]1[CH2:12][CH2:13][CH2:14][O:9][CH:10]1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[S:22][C:23]3[CH:29]=[C:28]([C:30]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[O:31])[CH:27]=[CH:26][C:24]=3[N:25]=2)=[C:17]([F:36])[CH:16]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 866387232-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamideHCID 178478984HCID 178478984, compound

Product 1

HCID 67111530(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Pyridylmagnesium chloride (3.92 mL, 2.84 mmol, solution in THF) was added to a solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide (0.52 g, 1.29 mmol) in THF (2 mL) and the reaction mixture was stirred for 30 min. Satd. NH4Cl (aq) was added and the mixture was extracted with DCM three times. The combined extracts were dried (MgSO4) and concentrated under vacuum to give (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone as a yellow solid. MS (ESI) m/z: Calculated: 420.1; Observed: 421.0 (M++1).

Workup

  1. extractionthe mixture was extracted with DCM three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8b5f47a4798c46c1b0d6b92d2d8f3fdb
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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