Diisopropylethylamine → HCID 178488473、化合物

HRID 1669848ノート

反応式

HRID 1669848 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[N:33]1[C:37]2[N:38]=CC=CC=2[N:35]=[N:34]1.C([N:45](CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.NC1NN=NN=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH:45][C:37]4[NH:38][N:35]=[N:34][N:33]=4)=[O:28])=[CH:25][CH:24]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

9

反応物 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733179PyBroPHCID 67335518HCID 67335518、化合物HCID 178509299HCID 178509299、化合物

生成物 1

HCID 178488473HCID 178488473、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

To a solution of the intermediate from step D (100 mg, 0.22 mmol) in 1:1 DMF/DCM (0.54 mL) was added 1-hydroxy-7-azabenzo-triazole (35 mg, 0.264 mmol), N,N-diisopropylethyl amine (92 μL, 0.53 mmol) amino tetrazole (56 mg, 0.66 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (51 mg, 0.26 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was checked by LC-MS and was found to have not gone to completion. An additional equivalent of amino tetrazole was added followed by Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (51 mg, 0.11 mmol). The reaction was complete in 3 hours. It was diluted with DCM (10 mL) and washed with 1N HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) to give the title compound. 1H NMR (DMSO, 500 MHz): δ 8.04 (d, J=8.5 Hz, 2H), 7.89 (d, J=2.1 Hz, 2H), 7.56 (t, J=1.9 Hz, 1H), 7.41 (d, J=8.7 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.14 (s, 1H), 7.05 (d, J=8.7 Hz, 2H), 5.53 (s, 2H), 3.79 (s, 3H). LC-MS: 2.53 min; (M+H)=520.2.

後処理

  1. waitThe reaction was left
  2. waitThe reaction was complete in 3 hours
  3. washwashed with 1N HCl
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC (Gilson)

出典と根拠

ORDレコード
ord-0dfa29b6c55c4df083ae10297f3c82f2
出典データセット
uspto-grants-2011_08
特許番号
US07989475B2

反応ノート

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