Water → HCID 178453011, compound

HRID 1171055Notes

Reaction equation

HRID 1171055 reaction equation
[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:32]=[CH:31][C:19]3[C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:21][O:22][C:18]=3[CH:17]=2)=[O:13])=[N+:5]([O-:10])[C:6](Cl)=[CH:7][CH:8]=1)#[N:2].[F:33][C:34]([F:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:35][NH2:36].C(Cl)Cl.O>CS(C)=O>[C:1]([C:3]1[C:4]([CH2:11][C:12]([NH:14][CH2:15][C:16]2[CH:32]=[CH:31][C:19]3[C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:21][O:22][C:18]=3[CH:17]=2)=[O:13])=[N+:5]([O-:10])[C:6]([NH:36][CH2:35][C:34]([F:43])([F:33])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 99641672,2-Difluoro-2-pyridin-2-ylethaneamineHCID 589729953-Cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-6-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide

Product 1

HCID 178453011HCID 178453011, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-cyano-6-chloro-2-[3-(tert-butoxycarbonyl)amino-benzo[d]isoxazol-6-ylmethyl]aminocarbonylmethyl-pyridine 1-oxide (29 mg) and 2,2-difluoro-2-pyridin-2-yl-ethylamine (20 mg) (Organic Process Research & Development 8:192-200, 2004), in DMSO (0.5 mL) was heated overnight at 80° C. LC/MS (ESI) indicated the mono-Boc product (M+H+ 580.1) as the major component. To the reaction vial was added DCM (10 mL) and water (3 mL). The mixture was vigorously stirred. After removing the aqueous layer, the organic layer was further washed with water (4×3 mL) to remove DMSO and water soluble components. Rotary evaporation of solvent afforded a syrupy residue that was used without purification. LCAMS (ESI) showed the mono-Boc product (M+H+ 580.1) as the major component and the di-Boc product (M+H+ 680.0) as a minor component.

Workup

  1. customAfter removing the aqueous layer
  2. washthe organic layer was further washed with water (4×3 mL)
  3. customto remove DMSO and water soluble components
  4. customRotary evaporation of solvent
  5. customafforded a syrupy residue that
  6. customwas used without purification

Sources & evidence

ORD record
ord-89d5d2acffb040948bf6a42a327d8fa4
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

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