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Diisopropylethylamine → HCID 58577101, 화합물

HRID 511193
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HRID 511193 반응식
[Li+].[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][CH2:18][C:19]([O-])=[O:20])[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.[NH:49]1[CH2:54][CH2:53][CH:52]([NH:55][C:56]2[CH:63]=[CH:62][C:59]([C:60]#[N:61])=[C:58]([C:64]([F:67])([F:66])[F:65])[CH:57]=2)[CH2:51][CH2:50]1.C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[F:67][C:64]([F:65])([F:66])[C:58]1[CH:57]=[C:56]([NH:55][CH:52]2[CH2:53][CH2:54][N:49]([C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([F:23])([F:2])[F:22])=[CH:9][CH:8]=4)[CH2:15][CH2:14]3)[CH2:50][CH2:51]2)[CH:63]=[CH:62][C:59]=1[C:60]#[N:61]
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 58576063HCID 58576063, 화합물HCID 66671763HCID 66671763, 화합물

생성물 1

HCID 58577101
HCID 58577101, 화합물
수율 70%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of 4-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-butyric acid lithium salt (16 mg; 0.05 mmol, prepared in accordance with Example 133) in tetrahydrofuran (1.0 mL) is added a solution of tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformamide (0.5 mL). 15 minutes later, a solution of 4-(piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile hydrochloride (15 mg; 0.05 mmol, prepared in accordance with Example 155) in dimethylformamide (10.5 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) is added. After 2 hours at room temperature, aluminium oxide (90 active basic) is added and stirring is continued. 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 (20 mg; 0.035 mmol). The structure was confirmed using Protocol I-D. Calculated mass=567; observed mass=567; HPLC retention time=2.17 min.

후처리

  1. customThe solids are removed by filtration
  2. concentrationthe filtrate is concentrated under high vacuum
  3. customThe obtained residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7f1ce4f640144e5e891d8bdca1370d31
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096524B2

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