Triethylamine → HCID 44177300, 화합물

HRID 1091880노트

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HRID 1091880 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-513af95e7be7456a98eb457ace261c1d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129390B2

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