Ethyl 2-formylcyclopropanecarboxylate → HCID 178468463, 화합물

HRID 555265

반응식

HRID 555265 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH:22]([CH:24]1[CH2:26][CH:25]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=O>CN1C(=O)CCC1>[CH2:30]([O:29][C:27]([CH:25]1[CH2:26][CH:24]1[C:22]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]([N:11]3[CH2:17][C:16]4([CH3:19])[CH2:18][CH:12]3[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]4)=[O:10])=[CH:3][C:2]=2[N:1]=1)=[O:28])[CH3:31]

참가 물질

4

반응물 2

HCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 66987132HCID 66987132, 화합물

생성물 1

HCID 178468463HCID 178468463, 화합물수율 8.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
50 °C

실험 절차

To a solution of (3,4-diaminophenyl)-(1,3,3-trimethyl-6-azabicyclo[3.2.1]oct-6-yl)methanone (500 mg, 1.74 mmol) in dry NMP (25 mL) at room temperature under an inert atmosphere of nitrogen was added approx. 500 mg of molecular sieve 4 Å followed by ethyl 2-formyl-1-cyclopropanecarboxylate (0.51 mL, 3.86 mmol). The mixture was stirred for 16 hrs at 50° C. The reaction was quenched by the addition of water (100 mL) followed by extraction with diethyl ether (3×100 mL). The combined organic phases were washed with water (3×100 mL), brine (100 mL), dried (MgSO4), filtered, and evaporated in vacuo. The resulting oil was purified by preparative HPLC, dried in vacuo at 50° C. affording 60 mg (8%) of the title compound as a solid. MS-ESI m/z 410; 1H NMR (400 MHz, CDCl3) δ 0.88-1.06 (m, 6H), 1.07-1.20 (m, 4H), 1.25 (t, 3H), 1.27-1.34 (m) and 1.49-1.66 (m, 3H), 1.36-1.48 (m, 2H), 1.72-1.84 (m, 2H), 2.36-2.48 (m, 1H), 2.66-2.76 (m, 1H), 3.18-3.27 (m, 1H), 3.30 (d) and 3.65 (d, 1H), 4.00-4.06 (m) and 4.57-4.65 (m, 1H), 4.14 (q, 2H), 7.18-7.30 (m, 2H), 7.57 (d, 1H), 10.37 (br s, 1H).

후처리

  1. customThe reaction was quenched by the addition of water (100 mL)
  2. extractionfollowed by extraction with diethyl ether (3×100 mL)
  3. washThe combined organic phases were washed with water (3×100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting oil was purified by preparative HPLC
  8. customdried in vacuo at 50° C.

출처 및 근거

ORD 기록
ord-3a8684624e734afa91e55e88544b4a25
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053431B2

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