Trimethyl orthoformate → HCID 86710193, 화합물

HRID 2284431노트

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HRID 2284431 반응식
[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][C:6]=2[N:7]=1.[OH:20][CH:21]([CH3:30])[C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23].C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]2[N:11]=[CH:10][C:9]([CH2:12][N:27]3[CH2:26][CH2:25][N:24]([C:22](=[O:23])[CH:21]([OH:20])[CH3:30])[CH2:29][CH2:28]3)=[CH:8][C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 13460159Piperazine, 1-(2-hydroxy-1-oxopropyl)- (9CI)HCID 86710192HCID 86710192, 화합물

생성물 1

HCID 86710193HCID 86710193, 화합물수율 35.6%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

In a 50 mL round bottom flask, 2-chloro-4-morpholinopyrido[3,2-d]pyrimidine-7-carbaldehyde (0.3 g, 0.0010 mol) and 1,2-dichloroethane (20 mL) were added. To the reaction flask, 2-hydroxy-1-(piperazin-1-yl)propan-1-one (0.204 g, 0.0013 mol) and trimethyl orthoformate (0.228 g, 0.0030 mol) were added and the reaction mixture stirred at room temperature for 12 hours. To the reaction mixture, sodium triacetoxyborohydride (g, 0.683 0.0020 mol) was added and stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to provide the crude product. The crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform) to provide the title compound (0.15 g, 33%). 1H NMR (300 MHz, CDCl3): δ 8.62 (d, J=1.8 Hz, 1H), 7.86 (d, J=1.2 Hz, 1H), 4.72 (br s, 4H), 3.84 (t, J=9.0 Hz, 4H), 3.65 (s, 2H), 3.60-3.52 (m, 1H), 3.41 (d, J=2.7 Hz, 1H), 3.23 (s, 4H), 2.46 (d, J=3.0 Hz, 4H), 1.27 (d, J=6.6 Hz, 3H): LC-MS (ESI): Calculated mass. 420.1, Observed mass [M+H]+: 421.1 (RT=0.24 min).

후처리

  1. stirringstirred at room temperature for 3 hours
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customto provide the crude product
  6. customThe crude product was purified by column chromatography (60-12 silica gel, 5% methanol in chloroform)

출처 및 근거

ORD 기록
ord-4bda41f29c4441d5ba2dd55927fcb93f
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145411B2

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