Diisopropylethylamine → N-{2-[(2-Dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-3-(4-trifluoromethyl-phenyl)-acrylamide

HRID 1174909

반응식

HRID 1174909 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:40][N:41]([CH3:56])[CH2:42][CH2:43][N:44]([CH3:55])[C:45]1[S:46][C:47]2[CH:53]=[C:52]([NH2:54])[CH:51]=[CH:50][C:48]=2[N:49]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CO>[CH3:40][N:41]([CH3:56])[CH2:42][CH2:43][N:44]([CH3:55])[C:45]1[S:46][C:47]2[CH:53]=[C:52]([NH:54][C:9](=[O:11])[CH:8]=[CH:7][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=3)[CH:51]=[CH:50][C:48]=2[N:49]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 55226563N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine

생성물 1

HCID 68774412N-{2-[(2-Dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-3-(4-trifluoromethyl-phenyl)-acrylamide수율 21.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Prepare according to Method A, using trans-4-trifluoromethylcinnamic acid (130 mg, 0.60 mmol), HATU (229 mg, 0.602 mmol), N2-(2-dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine (100 mg, 0.400 mmol), DIEA (260 μL, 1.49 mmol), and a chromatography gradient of MeOH in CH2Cl2 (8-20%) to afford the title compound (38 mg, 21%). mass spectrum (m/e): 449.0 [M+H], 447.0 [M−H]. 1H NMR (400 MHz, DMSO-d6): δ 10.50 (s, 1H), 8.31 (d, 1H, J=2.2 Hz), 7.87-7.78 (m, 4H), 7.64 (d, 1H, J=15.8 Hz), 7.52 (dd, 1H, J=8.8, 2.2 Hz), 7.44 (d, 1H, J=8.8 Hz), 7.03 (d, 1H, J=15.8 Hz), 3.97 (dd, 2H, J=6.4, 6.4 Hz), 3.39 (dd, 2H, J=6.2, 6.2 Hz), 3.13 (s, 3H), 2.85 (s, 6H).

후처리

  1. customPrepare

출처 및 근거

ORD 기록
ord-86ae20dce964483ca460d6035cc45da9
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07838543B2

연결된 노트

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