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Cesium carbonate → 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

HRID 2036662
ノート
印刷プレビュー

反応式

HRID 2036662 の反応式
[NH2:1][C@H:2]([C:4]1[N:8]([CH:9]2[CH2:11][CH2:10]2)[C:7]2[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[CH:13][CH:14]=[CH:15][C:6]=2[N:5]=1)[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:26][C:27]1[S:28][C:29](Br)=[N:30][N:31]=1>CCO>[NH2:26][C:27]1[S:28][C:29]([NH:1][C@H:2]([C:4]2[N:8]([CH:9]3[CH2:10][CH2:11]3)[C:7]3[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[CH:13][CH:14]=[CH:15][C:6]=3[N:5]=2)[CH3:3])=[N:30][N:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 58459136(S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide

生成物 1

HCID 584591982-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of (S)-2-(1-aminoethyl)-1-cyclopropyl-N-methyl-1H-benzo[d]imidazole-7-carboxamide (prepared in example 20) (63.5 mg, 0.25 mmol), cesium carbonate (80 mg, 0.25 mmol) and 2-amino-5-bromo-[1,3,4]thiadiazole (44.3 mg, 0.25 mmol) in EtOH (5 mL) under N2 was stirred at rt for 18 h. The reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, washed with water, brine, dried over magnesium sulfate, and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using 0 to 10% gradient of MeOH in DCM with 0.2% NH4OH as eluent to give 2-((1S)-1-((5-amino-1,3,4-thiadiazol-2-yl)amino)ethyl)-1-cyclopropyl-N-methyl-1H-benzimidazole-7-carboxamide: 1H NMR (400 MHz, DMSO-d6) δ 8.46-8.39 (1H, m); 7.62 (1H, d, J=8.0 Hz), 7.44 (1H, d, J=8.0 Hz), 7.24-7.16 (2H, m); 6.22 (2H, s), 5.46-5.37 (1H, m), 3.40-3.30 (1H, m), 2.82 (3H, d, J=4.0 Hz), 1.55 (3H, d, J=4.0 Hz), 1.22-1.15 (1H, m), 1.12-1.04 (1H, m), 1.01-0.92 (1H, m), 0.83-0.74 (1H, m); LC-MS (ESI) m/z 358.0 [M+H]+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-ec6c36cc856a464e9a683f8c706adc11
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575183B2

反応ノート

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