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Diisopropylethylamine → HCID 68157707、化合物

HRID 243432
ノート
印刷プレビュー

反応式

HRID 243432 の反応式
Cl.Cl.[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([C@@H:12]([NH2:14])[CH3:13])[N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1.Cl[C:23]1[C:28]([C:29]#[N:30])=[C:27]([CH3:31])[N:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C>C(O)(C)C.CCOC(C)=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([C@@H:12]([NH:14][C:23]3[C:28]([C:29]#[N:30])=[C:27]([CH3:31])[N:26]=[CH:25][CH:24]=3)[CH3:13])[N:9]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]=2[CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 67125855HCID 67125855、化合物HCID 68157580(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride

生成物 1

HCID 68157707HCID 68157707、化合物収率 24.6%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethylamine dihydrochloride (0.083 g, 0.25 mmol), 4-chloro-2-methylnicotinonitrile (0.035 g, 0.23 mmol) and diisopropylethylamine (0.160 mL, 0.92 mmol) in isopropanol (1 mL) was heated to 80° C. in a sealed tube under argon for 2 h then at 75° C. for 86 h. The reaction mixture was cooled, diluted with EtOAc (20 mL) and washed with water (10 mL). The organic extracts were dried (Na2SO4), evaporated to dryness and purified by column chromatography (Si—PCC, gradient 0-8% (9:1 MeOH/0.880 NH3) in DCM). Product containing fractions were evaporated and freeze dried to give 340 as a pale brown solid, (21 mg, 24%). LCMS (Method C): RT 3.11 min [M+H]+ 372.08. 1H NMR δ (ppm DMSO-d6): 7.98 (1H, d, J=6.15 Hz), 7.77 (1H, dd, J=8.82, 4.86 Hz), 7.52-7.50 (5H, m), 7.12-7.11 (2H, m), 6.85 (1H, dd, J=8.91, 2.51 Hz), 6.40 (1H, d, J=6.24 Hz), 5.11 (1H, dq, J=7.04 Hz), 2.41 (3H, s), 1.56 (3H, d, J=6.64 Hz)

後処理

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water (10 mL)
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. customevaporated to dryness
  5. custompurified by column chromatography (Si—PCC, gradient 0-8% (9:1 MeOH/0.880 NH3) in DCM)
  6. additionProduct containing fractions
  7. customwere evaporated
  8. customfreeze dried

出典と根拠

ORDレコード
ord-c61e3453d81c44f9b2e010c49c026f78
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653089B2

反応ノート

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