Pyridine → HCID 66581050, compound

HRID 1521843Notes

Reaction equation

HRID 1521843 reaction equation
[N:1]1([C:7]([C:9]2[C:13]([NH2:14])=[CH:12][N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35].[NH4+].[Cl-]>C(Cl)Cl>[Br:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([NH:14][C:13]1[C:9]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])=[N:10][N:11]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 5204032-Bromobenzenesulfonyl chlorideHCID 66578900HCID 66578900, compound

Product 1

HCID 66581050HCID 66581050, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(morpholin-4-ylcarbonyl)-1-phenyl-1H-pyrazol-4-amine (260 mg; 0.95 mmol; 1 eq.) in DCM (10 mL) is added pyridine (151 μL; 1.91 mmol; 2.00 eq.) and 2-bromobenzene-1-sulfonyl chloride (317 mg; 1.24 mmol; 1.30 eq.). The reaction is stirred for 48 h at room temperature. After this time, DCM is added to the reaction mixture which is ished with NH4Cl sat, dried over MgSO4 and purified by flash chromatography (AcOEt/heptane 4:1) to give 440 mg (94%) of the title compound as a white solid. 1H NMR (DMSO) δ 9.93 (s, 1H), 8.43 (s, 1H), 8.11-8.02 (m, 1H), 7.91-7.84 (m, 1H), 7.84-7.76 (m, 2H), 7.59-7.45 (m, 4H), 7.40-7.31 (m, 1H), 3.81-3.69 (m, 2H), 3.67-3.49 (m, 6H) HPLC (max plot) 94.6%; Rt 4.83 min. MS (ESI+): 493.2.

Workup

  1. dry with materialdried over MgSO4
  2. custompurified by flash chromatography (AcOEt/heptane 4:1)

Sources & evidence

ORD record
ord-7a1377d953264374a873d0324d4c3b1d
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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