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Phenyl 5-cyanopyrazin-2-ylcarbamate → tert-Butyl 2-(2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)phenoxy)ethyl(2,4-difluorobenzyl)carbamate

HRID 1019739
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HRID 1019739 반응식
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([Cl:28])[CH:3]=1.[C:29]([C:31]1[N:32]=[CH:33][C:34]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)=[N:35][CH:36]=1)#[N:30]>CN(C)C=O>[Cl:28][C:4]1[CH:3]=[C:2]([NH:1][C:38]([NH:37][C:34]2[CH:33]=[N:32][C:31]([C:29]#[N:30])=[CH:36][N:35]=2)=[O:39])[CH:27]=[CH:26][C:5]=1[O:6][CH2:7][CH2:8][N:9]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]
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4

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HCID 22064357Phenyl 5-cyanopyrazin-2-ylcarbamateHCID 67469270tert-Butyl 2-(4-amino-2-chlorophenoxy)ethyl(2,4-difluorobenzyl)carbamate

생성물 1

HCID 67469007tert-Butyl 2-(2-chloro-4-(3-(5-cyanopyrazin-2-yl)ureido)phenoxy)ethyl(2,4-difluorobenzyl)carbamate수율 26%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of tert-butyl 2-(4-amino-2-chlorophenoxy)ethyl(2,4-difluorobenzyl)-carbamate (1.6 g, 3.87 mmol) in N,N-dimethylformamide (4 mL) at RT were phenyl 5-cyanopyrazin-2-ylcarbamate (1.39 g, 5.81 mmol) (Example 10) and N,N,N-diisopropylethylamine (0.751 g, 5.81 mmol) added. The reaction mixture was heated at 60° C. for 1.5 hours then the reaction mixture was poured into ice-water (100 mL) and allowed to stand for 30 minutes. The resulting precipitate was collected, washed with water and air dried. The crude product was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM to give the title compound (0.53 g, 26% yield).

후처리

  1. customat RT
  2. additionadded
  3. customThe resulting precipitate was collected
  4. washwashed with water and air
  5. customdried
  6. customThe crude product was purified by column chromatography on neutral silica gel using 0-2% methanol in DCM

출처 및 근거

ORD 기록
ord-a9169ecee8d54eac94e7e15b2504a5bc
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716287B2

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