4-Methylmorpholine → HCID 86699514, compound

HRID 1497565Notes

Reaction equation

HRID 1497565 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[CH3:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](O)=[O:15].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>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:14](=[O:15])[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH3:10])[NH2:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 113702-Methoxybenzoic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 86699514HCID 86699514, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-hydrazinylpyridine (7.1 g, 38 mmol) and 2-methoxybenzoic acid (7.0 g, 46 mmol) in dichloromethane (DCM, 100 mL) were added benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, 25.2 g, 57 mmol) and N-methylmorpholine (NMM, 13.4 g, 0.10 mol), and it was stirred at room temperature for 2 h. The mixture was filtered and the solids were washed with DCM (50 mL×3), dried to give the title compound (8.23 g, 67.5% yield) as yellow solids. MS: m/z 322.1 [M+H+].

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids were washed with DCM (50 mL×3)
  3. customdried

Sources & evidence

ORD record
ord-d643452b348a41d1a618703e9e55d994
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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