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Diisopropylethylamine → HCID 58577219, 화합물

HRID 511194
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HRID 511194 반응식
[Li+].[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=C[C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([O-:21])=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.F[P-](F)(F)(F)(F)F.C[N:32](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:21])[CH2:18][CH2:17][CH2:16][N:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:22])[F:23])=[CH:9][N:32]=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 585760704-[4-(4-Trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid lithium saltHCID 66671763HCID 66671763, 화합물

생성물 1

HCID 58577219
HCID 58577219, 화합물
수율 32%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred suspension of 4-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-butyric acid lithium salt (17 mg; 0.05 mmol, prepared in accordance with Example 3) in tetrahydrofuran (1.0 mL) is added 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 (0.5 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 stiffing 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 (9 mg; 0.016 mmol). The structure was confirmed using Protocol I-D. Calculated mass=569; observed mass=569; HPLC retention time=1.48 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-4263852b88cb46c78a85689ccb914140
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096524B2

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