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

HRID 1922427노트

반응식

HRID 1922427 반응식
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

참가 물질

5

반응물 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

생성물 1

HCID 178480394HCID 178480394, 화합물수율 82%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cf8f3b2fea60439abbea22bd67a9526c
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

반응 노트

불러오는 중…