Potassium Carbonate → HCID 178419006、化合物

HRID 1582262ノート

反応式

HRID 1582262 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH2:30])[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.C(OC([NH:38][C:39](N1C=CC=N1)=[N:40]C(OC(C)(C)C)=O)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.[NH4+].[Cl-]>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH:30][C:39]([NH2:40])=[NH:38])[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 21984983(1H-Benzimidazol-2-ylmethyl)-(2-Aminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

生成物 1

HCID 178419006HCID 178419006、化合物収率 92.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of (1H-Benzimidazol-2-ylmethyl)-(2-Aminomethyl-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (see AMD9720) (50 mg, 0.125 mmol) in THF (5 mL) was added added N,N′-di-t-butoxycarbonyl-pyrazole-1-carboxamidine (60 mg, 0.187 mmol) and potassium carbonate (35 mg, 0.25 mmol) and the mixture stirred overnight. The reaction was diluted with aqueous NH4Cl (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were dried (Na2SO4), concentrated and purified by chromatography on silica gel (5% MeOH/CH2Cl2) to give the desired product as a pale foam (51 mg, 64%). 1H NMR (CDCl3) δ1.47 (s, 9H), 1.48 (s, 9H), 1.81 (m, 1H), 2.00 (m, 2H), 2.26 (m, 2H), 2.71-2.88 (m, 2H), 3.89-4.05 (m, 5H), 4.73 (dd, 1H, J=15.5, 5.1 Hz), 4.96 (dd, 1H, J=15.5, 5.7 Hz), 7.12 (m, 7H), 7.36-7.44 (m, 3H), 7.55 (br s, 1H (NH)), 8.55 (m, 1H (NH)), 8.66 (d, 1H, J=5.1 Hz).

後処理

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by chromatography on silica gel (5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-34acd8035871416cbc928d8f0e63a735
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

反応ノート

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