4-Methylmorpholine → HCID 67599708, compound

HRID 1497577Notes

Reaction equation

HRID 1497577 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:5][N:4]=1)[NH2:2].[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[C:20]([O:27][CH3:28])[CH:19]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>C(Cl)Cl>[Cl:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:2][NH:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=3)=[CH:5][N:4]=2)=[O:23])=[C:20]([O:27][CH3:28])[CH:19]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 936824-Chloro-o-anisic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 20300086HCID 20300086, compound

Product 1

HCID 67599708HCID 67599708, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydrazinyl-5-(4-methoxyphenyl)pyridine (200 mg, 0.93 mmol), 4-chloro-2-methoxybenzoic acid (210 mg, 1.12 mmol), BOP (500 mg, 1.12 mmol) and NMM (330 mg, 3.27 mmol) in DCM (9 mL) was stirred at room temperature under Nitrogen overnight. The resulting mixture was filtered, and the solid was washed with DCM, dried to give the title compound as white solids (290 mg, 81.2% yield), which was used for the next reaction without further purification. MS: m/z 384.2 [M+H+].

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe solid was washed with DCM
  3. customdried

Sources & evidence

ORD record
ord-da6d6b1c95ce4075a385e156830c22b4
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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