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Methylamine → HCID 178485040、化合物

HRID 2189951
ノート
印刷プレビュー

反応式

HRID 2189951 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]([C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]=[C:7]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:6]1.C(N(CC)CC)C.C1C=CC(O[C:44](OC2C=CC=CC=2)=[N:45][C:46]#[N:47])=CC=1.[CH3:55][NH2:56]>CC(O)C.CO>[C:55](/[N:47]=[C:46](/[NH:45][CH3:44])\[NH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]([C:10](=[O:15])[C:11]([CH3:14])([CH3:12])[CH3:13])[N:8]=[C:7]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:6]1)#[N:56]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 601398321-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one

生成物 1

HCID 178485040HCID 178485040、化合物収率 41%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 3776Isopropanol溶媒

実験手順

1-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one (66 mg, 0.158 mmol) was weighed into a flask, then dissolved in 2.0 mL IPA. Triethylamine (0.055 ml, 0.38 mmol) was then added followed by diphenyl cyanocarbonimidate (75 mg, 0.316 mmol). The reaction was then stirred at room temperature for 1.5 hours. The reaction was then transferred to a scaled tube, followed by addition of 3 mL of methyl amine (2.4 ml, 4.9 mmol) in MeOH. The reaction was then placed in a 60° C. bath for 12 hours. The reaction vas then removed and concentrated, and the residue was purified by flash column chromatography (3-7% MeOH/CH2Cl2) to provide the desired product (32 mg, 41%) as a light orange foam film. MS ESI (+) m/z 499 (M+E) detected; 1H NMR (400 MHz, MeOH) δ 7.48 (m, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.38 (m, 2H), 7.28 (m, 3H), 3.45 (m, 1H), 3.39 (m, 1H), 3.27 (m, 1H), 2.78 (s, 3H), 2.45 (m, 1H), 1.99 (m, 1H), 1.59 (m, 1H), 1.39 (s, 9H).

後処理

  1. customThe reaction was then transferred to a scaled tube
  2. customwas then placed in a 60° C.
  3. customfor 12 hours
  4. customThe reaction vas
  5. customthen removed
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (3-7% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-0df3a7af2aa440b2818ce5d312c24598
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324257B2

反応ノート

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