Triethylamine → HCID 44177300, 화합물

HRID 340397노트

반응식

HRID 340397 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:26][CH2:25][C:14]2[NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22](O)=[O:23])=[CH:20][C:21]=3[C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[NH2:53][CH:54]1[CH2:59][CH2:58][N:57]([CH2:60][C:61]2[CH:66]=[CH:65][C:64]([C:67]#[N:68])=[CH:63][CH:62]=2)[CH2:56][CH2:55]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)C.CO.C(Cl)Cl.C(Cl)Cl>[C:67]([C:64]1[CH:65]=[CH:66][C:61]([CH2:60][N:57]2[CH2:58][CH2:59][CH:54]([NH:53][C:22]([C:19]3[CH:18]=[CH:17][C:16]4[NH:15][C:14]5[CH2:25][CH2:26][N:11]([C:9]([O:8][CH2:1][C:2]6[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=6)=[O:10])[CH2:12][C:13]=5[C:21]=4[CH:20]=3)=[O:23])[CH2:55][CH2:56]2)=[CH:62][CH:63]=1)#[N:68]

참가 물질

10

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44120478HCID 44120478, 화합물HCID 57750052HCID 57750052, 화합물

생성물 1

HCID 44177300HCID 44177300, 화합물

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 21226129Dichloromethane methanol용매

실험 절차

To a solution of 2-(benzyloxycarbonyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (3, 0.5 g, 1.4 mmol) in DMF (10 mL), HATU (0.65 g, 1.7 mmol), 4-amino-1-(4-cyanobenzyl)piperidine dihydrochloride (0.41 g, 1.4 mmol) and triethylamine (1.05 mL, 0.76 g, 7.5 mmol) were added. The resulting reaction mixture was allowed to stir at room temperature overnight, poured into saturated sodium bicarbonate solution (75 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (2×30 mL), brine (1×30 mL), dried (MgSO4), filtered and concentrated to give a tan solid. Column chromatography (neat DCM→5% MeOH/DCM) provided benzyl 8-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (4a in Scheme 1(b)) as a white solid upon trituration with ethyl ether (0.55 g, 70%). 1H NMR (DMSO-d6, 300 MHZ) 11.14 (br s, 1H), 8.04 (d, J=8.0 Hz, 1H), 8.00 (s, 1H), 7.79 (d, J=8.0 Hz, 2H), 7.59 (d, J=8.5 Hz, 1H), 7.51 (d, J=7.7 Hz, 2H), 7.39-7.27 (m, 6H), 5.14 (s, 2H), 4.67 (br s, 2H), 3.80 (br s, 3H), 3.57 (s, 2H), 2.82 (br s, 4H), 2.08 (t, J=11.0 Hz, 2H), 1.80 (d, J=11.3 Hz, 2H), 1.61 (q, J=10.7 Hz, 2H) ppm; MS (ES) 548 (M+H).

후처리

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with water (2×30 mL), brine (1×30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a tan solid

출처 및 근거

ORD 기록
ord-0f503e6b04b548f095b1b2f2f71602f5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895578B2

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