N,N-Diethyl-2-propanamine → HCID 25099396, 화합물

HRID 2381991노트

반응식

HRID 2381991 반응식
C(N(CC)C(C)C)C.[C:9]1([C:15]2[N:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[F:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([NH2:34])[CH:29]=[CH:28]2>C(Cl)Cl>[F:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([NH:34][C:21]([C:18]1[CH:17]=[N:16][C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:20][CH:19]=1)=[O:22])[CH:29]=[CH:28]2

참가 물질

5

반응물 3

HCID 521913N,N-Diethyl-2-propanamineHCID 106326372-phenylpyrimidine-5-carbonyl ChlorideHCID 450786905-Fluoro-1H-indol-1-amine

생성물 1

HCID 25099396HCID 25099396, 화합물수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl-iso-propylamine (2.30 mmol) is added to a stirred solution of 2-phenyl-pyrimidine-5-carboxylic acid chloride (1.15 mmol) and 5-fluor-indol-1-ylamine (1.15 mmol) in DCM (20 mL) at rt. The reaction mixture is stirred at rt overnight and concentrated in vacuo. The residue is dissolved in EtOAc (30 mL), then washed with 5% HCl (10 mL), water (10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10-40% EtOAc in heptane to afford 2-phenyl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide (185 mg, 49%) as a solid. MS: 333 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.56 (s, H) 7.02 (m, H), 7.10-7.38 (m, 4H), 7.55 (s, 3H), 8.53 (s, 2H), 8.70-9.40 (br, 2H). IC50=3 nM.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc (30 mL)
  3. washwashed with 5% HCl (10 mL), water (10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 10-40% EtOAc in heptane

출처 및 근거

ORD 기록
ord-2e49c209c1e64ce8b3f1c2b179dcf037
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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