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Cyclopropanemethanamine → 2-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide

HRID 985323
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HRID 985323 반응식
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:27](O)=[O:28].[NH2:30][CH2:31][CH:32]1[CH2:34][CH2:33]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH:32]1([CH2:31][NH:30][C:27]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:17]=[CH:16][N:15]=[C:14]5[CH:18]=[C:19]([C:21]6[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=6)[S:20][C:13]=45)=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])=[O:28])[CH2:34][CH2:33]1
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참가 물질

5

반응물 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221435462-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid

생성물 1

HCID 20767915
2-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid (cyclopropylmethyl)amide
수율 81.2%

실험 절차

This material was prepared from the reaction of 2-methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid 117b (70 mg, 0.166 mmole), (aminomethyl)cyclopropane (43 μL, 0.50 mmole) and diisopropylethylamine (58 μL, 0.33 mmole), and HBTU (94 mg, 0.25 mmole) in a manner similar to that previously described for example 117 to afford a pale yellow solid (64 mg, 53%). 1H NMR (DMSO-d6, 300 MHz) δ8.61 (1H, d, J=5.46 Hz), 8.49 (1H, t, J=5.65 Hz), 8.07 (1H, s), 7.99 (1H, d, J=2.26 Hz), 7.85 (1H, d, J=8.67 Hz), 7.63 (1H, s), 7.37 (1H, s), 7.36 (1H, dd, J=2.4, 8.67 Hz), 6.81 (1H, d, J=5.65 Hz), 4.01 (3H, s), 3.20 (2H, t, J=6.31 Hz), 2.62 (3H, s), 1.08 (1H, m), 0.47 (2H, m), 0.27 (2H, m).

출처 및 근거

ORD 기록
ord-36dba9d2a044496a8d01cef4d2057e2b
출처 데이터셋
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06869962B2

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