Hydrochloride methanol → 3-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine

HRID 1713446ノート

反応式

HRID 1713446 の反応式
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=[C:9]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[S:8]1)=[N+]=[N-].Cl.CO>CO.[Pd]>[F:29][C:23]1[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=1[C:9]1[S:8][C:7]([CH2:6][CH2:5][CH2:4][NH2:1])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=1

参加物

5

反応物 2

HCID 21893726Hydrochloride methanolHCID 866087732-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

生成物 1

HCID 119599503-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine収率 61.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (0.046 g, 0.090 mmol) in 2 mL of methanol was added 1N HCl/MeOH (0.27 mL, 0.27 mmol) followed by 10% Pd/C (10 mg). The mixture was hydrogenated under a balloon atmosphere for 1 hour then filtered through GF paper and the filtrate concentrated in vacuo. The residue was triturated with diethyl ether, filtered, washed with ether and dried in vacuo to afford the desired product as a bright yellow solid (0.027 g, 50%). MS ESI (+) m/z 486 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 1H), 7.45 (d, 2H, J=7.6 Hz), 7.32 (m, 2H), 7.26 (m, 1H), 7.06 (m, 2H), 3.50 (m, 2H), 3.43 (m, 1H), 2.77 (t, 2H, J=6.9 Hz), 2.68 (m, 2H), 2.56 (m, 2H), 2.46 (s, 3H), 2.41 (m, 1H), 1.99 (m, 1H), 1.55 (m, 1H) ppm.

後処理

  1. filtrationthen filtered through GF paper
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-510a6c48a0f644ac8a428c3683cafb41
出典データセット
uspto-grants-2010_09
特許番号
US07795282B2

反応ノート

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