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Trifluoroacetic acid → N-Benzyl-6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxamide Trifluoroacetate

HRID 541942
ノート
印刷プレビュー

反応式

HRID 541942 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:26](O)=[O:27])[CH:10]=[C:11]([CH:25]=3)[O:12][CH2:13][CH2:14][S:15][C:16]3[CH:24]=[C:20]([NH:21][C:22]=1[N:23]=2)[CH:19]=[CH:18][CH:17]=3.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:70]([OH:76])([C:72]([F:75])([F:74])[F:73])=[O:71]>CN(C)C=O.CO>[F:73][C:72]([F:75])([F:74])[C:70]([OH:76])=[O:71].[CH2:29]([NH:36][C:26]([C:9]1[CH:10]=[C:11]2[CH:25]=[C:7]([CH:8]=1)[NH:6][C:5]1=[N:23][C:22](=[C:2]([Cl:1])[CH:3]=[N:4]1)[NH:21][C:20]1=[CH:24][C:16](=[CH:17][CH:18]=[CH:19]1)[S:15][CH2:14][CH2:13][O:12]2)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579621096-Chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylic Acid

生成物 1

HCID 69016243
N-Benzyl-6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxamide Trifluoroacetate
収率 16%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
20 °C

実験手順

A solution of 6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylic acid (30 mg, 72 μmol) and benzylamine (12 μL, 0.11 mmol) in N,N-dimethylformamide (1 mL) was treated with N,N-diisopropylethylamine (50 μL, 0.29 mmol) followed by 0.5 M O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate in N,N-dimethylformamide (0.19 mL, 94 μmol) and stirred at 20° C. for 16 h. The reaction mixture was diluted with methanol (4.9 mL) and TFA (0.1 mL) and the resultant suspension was filtered. The filtrate was purified by preparative LCMS to give the desired product (7 mg, 16%) as a solid. LCMS for C26H23ClN5O2S (M+H)+: m/z=503.9. 1H NMR (300 MHz, DMSO-d6): δ 9.66 (s, 1H), 8.91-8.88 (m, 2H), 8.18 (s, 1H), 7.96 (d, J=5.6 Hz, 2H), 7.37-7.21 (m, 9H), 6.94 (s, 1H), 4.41 (d, J=5.9 Hz, 2H), 4.16-4.11 (m, 2H), 3.28-3.23 (m, 2H).

後処理

  1. filtrationthe resultant suspension was filtered
  2. customThe filtrate was purified by preparative LCMS

出典と根拠

ORDレコード
ord-8d3d293e6185454fb553c82f2abb9795
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08871753B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート