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Diisopropylethylamine → HCID 58576863, 화합물

HRID 511166
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HRID 511166 반응식
[Li+].[F:2][C:3]([F:22])([F:21])[C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]([O-:20])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.F[P-](F)(F)(F)(F)F.CN(C)C(ON1C2C=CC=CC=2N=N1)=[N+](C)C.Cl.[N+:48]([C:51]1[CH:56]=[CH:55][C:54]([NH:57][CH:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)=[CH:53][C:52]=1[C:64]([F:67])([F:66])[F:65])([O-:50])=[O:49].C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>CN(C)C=O.O1CCCC1>[N+:48]([C:51]1[CH:56]=[CH:55][C:54]([NH:57][CH:58]2[CH2:59][CH2:60][N:61]([C:18](=[O:20])[CH2:17][CH2:16][N:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:8]=[N:9][C:4]([C:3]([F:2])([F:22])[F:21])=[CH:5][CH:6]=4)[CH2:15][CH2:14]3)[CH2:62][CH2:63]2)=[CH:53][C:52]=1[C:64]([F:67])([F:65])[F:66])([O-:50])=[O:49]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 58576136HCID 58576136, 화합물HCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

생성물 1

HCID 58576863
HCID 58576863, 화합물
수율 54%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

3-[4-(6-Trifluoromethyl-pyridin-3-yl)-piperazin-1-yl]-propionic acid lithium salt (15 mg; 0.05 mmol, prepared in accordance with Example 125) and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) are diluted in a 2 to 1 mixture of dimethylformamide and tetrahydrofuran (0.75 mL). A solution of (4-nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride (16 mg; 0.05 mmol, prepared in accordance with Example 8) in dimethylformamide (0.25 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) are added and the reaction is then stirred. After 4 hours at room temperature, aluminium oxide (90 active basic) is added and stiffing is continued for 40 minutes. The solids are removed by filtration and the filtrate is concentrated under high vacuum. The obtained residue is purified by preparative HPLC to afford the desired compound (16 mg; 0.027 mmol). The structure was confirmed using Protocol I-D. Calculated mass=574; observed mass=575; HPLC retention time=1.42 min.

후처리

  1. waitstiffing is continued for 40 minutes
  2. customThe solids are removed by filtration
  3. concentrationthe filtrate is concentrated under high vacuum
  4. customThe obtained residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f3ed1ed80d2147bcaa8eb450b9bb65b7
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096524B2

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