Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → HCID 178480394、化合物

HRID 1922427ノート

反応式

HRID 1922427 の反応式
CN([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=O)C(=O)OC1C=CC=CC=1.NC1C=[C:36]2[C:41](=CC=1)[N:40]([CH2:44]CN(C)C(=O)OC1C=CC=CC=1)[C:39](=O)[CH2:38]C2>C(O)C.C([O-])(O)=O.[Na+]>[CH3:44][N:40]1[CH2:41][CH2:36][CH:15]([N:14]2[CH2:13][CH2:12][CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([NH:24][C:25]([C:27]4[S:28][CH:29]=[CH:30][CH:31]=4)=[NH:26])[CH:21]=[CH:22][C:23]2=3)[CH2:38][CH2:39]1

参加物

5

反応物 2

HCID 59807067Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

生成物 1

HCID 178480394HCID 178480394、化合物収率 82%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of compound 8 (321.6 mg, 1.24 mmol) in dry ethanol (10 mL) was treated with compound 6 (707 mg, 2.48 mmol) at room temperature. The reaction mixture was stirred for 16 hours at room temperature then diluted with saturated NaHCO3 solution (50 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (Na2SO4) and concentrated to give a brown residue. The crude product was purified by column chromatography on silica gel (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2, 4:96 to 5:95) to give compound 39 (374.6 mg, 81.9%) as a yellow residue. 1H-NMR (DMSO-d6) δ 1.56-1.79 (m, 9H), 1.97 (t, 2H, J=10.5 Hz), 2.16 (s, 3H), 2.65 (brs, 2H), 2.80 (d, 2H, J=10.2 Hz), 2.91 (brs, 2H), 3.12 (m, 1H), 6.30 (brs, 2H), 6.59 (m, 2H), 6.89 (d, 1H, J=8.9 Hz), 7.07 (t, 1H, J=4.5 Hz), 7.57 (d, 1H, J=5.1), 7.70 (d, 1H, J=3.5 Hz); ESI-MS (m/z, %) 369 (MH+, 35), 272 (100). ESI-HRMS calculated for C21H29N4S (MH+), calculated: 369.2101; observed: 369.2107; HPLC-purity: 97.31% by area.

後処理

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined organic fractions were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a brown residue
  6. customThe crude product was purified by column chromatography on silica gel (MeOH:CH2Cl2, 2:98 followed by 2 N NH3 in MeOH:CH2Cl2, 4:96 to 5:95)

出典と根拠

ORDレコード
ord-cf8f3b2fea60439abbea22bd67a9526c
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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