Water → HCID 178453011, 화합물

HRID 1171055노트

반응식

HRID 1171055 반응식
[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]

참가 물질

6

반응물 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

생성물 1

HCID 178453011HCID 178453011, 화합물

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-89d5d2acffb040948bf6a42a327d8fa4
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829584B2

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