Triethylamine → HCID 44177300、化合物

HRID 1042530ノート

反応式

HRID 1042530 の反応式
[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]

参加物

10

反応物 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、化合物HCID 57750052HCID 57750052、化合物

生成物 1

HCID 44177300HCID 44177300、化合物

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-02d56a3010814bcca562d93ac6be5a3b
出典データセット
uspto-grants-2013_10
特許番号
US08557822B2

反応ノート

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