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L-(+)-Cysteine → S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine

HRID 715841
ノート
印刷プレビュー

反応式

HRID 715841 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH2:24][C:25]5([CH3:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:23]=4)=[CH:17][CH:18]=3)=[O:13])=[CH:6][C:5]=12.CN1CC[O:36][CH2:35][CH2:34]1.BrCC(ON1C(=O)CCC1=O)=O.[NH2:51][C@@H:52]([CH2:56][SH:57])[C:53]([OH:55])=[O:54]>C(N(CC)C(C)C)(C)C.O.C(O)(C(F)(F)F)=O>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([C:14]3[S:15][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH2:24][C:25]5([CH3:31])[CH2:30][CH2:29][N:28]([C:35](=[O:36])[CH2:34][S:57][CH2:56][C@@H:52]([C:53]([OH:55])=[O:54])[NH2:51])[CH2:27][CH2:26]5)[CH:23]=4)=[CH:17][CH:18]=3)=[O:13])=[CH:6][C:5]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 5862L-(+)-CysteineHCID 79724-MethylmorpholineHCID 3565210N-succinimidyl bromoacetateHCID 86702099N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide

生成物 1

HCID 86702100S-(2-{4-[(4-{5-[(imidazo[1,2-a]pyridin-7-ylmethyl)carbamoyl]thiophen-2-yl}-1H-pyrazol-1-yl)methyl]-4-methylpiperidin-1-yl}-2-oxoethyl)-L-cysteine

試薬・触媒・溶媒 3

HCID 6422Trifluoroacetic acid触媒HCID 962Water溶媒HCID 81531Diisopropylethylamine溶媒2 回

実験手順

A suspension of N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-{1-[(4-methylpiperidin-4-yl)methyl]-1H-pyrazol-4-yl}thiophene-2-carboxamide (0.100 g, 0.197 mmol) and 4-methylmorpholine (0.108 ml, 0.985 mmol) in N,N-diisopropylethylamine (0.5 ml) was added to 2,5-dioxopyrrolidin-1-yl 2-bromoacetate (0.056 g, 0.236 mmol) in N,N-diisopropylethylamine (0.5 ml) and stirred at room temperature. After 1 hour, (R)-2-amino-3-mercaptopropanoic acid (0.119 g, 0.985 mmol) as a solution in water (1 ml) was added. After stirring an additional 1 hour, a few drops of TFA were added to form a homogeneous solution which was purified by revere phase chromatography. The product containing peaks were lyophilized to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (t, J=6.0 Hz, 1H), 8.86 (d, J=7.0 Hz, 1H), 8.44 (bs, 2H), 8.32 (d, J=2.0 Hz, 1H), 8.18-8.11 (m, 2H), 7.86-7.77 (m, 3H), 7.46 (dd, J=7.0, 1.5 Hz, 1H), 7.27 (dd, J=3.7, 1.8 Hz, 1H), 4.65 (d, J=5.8 Hz, 2H), 4.21-4.13 (m, 1H), 4.13-4.02 (m, 2H), 4.02-3.92 (m, 1H), 3.87-3.57 (m, 3H), 3.42-3.29 (m, 1H), 3.29-3.18 (m, 1H), 3.10 (dd, J=14.6, 4.7 Hz, 1H), 2.98 (dd, J=14.6, 7.6 Hz, 1H), 1.60-1.18 (m, 4H), 0.96 (s, 3H); MS (ESI(+)) m/e 596 (M+H)+.

後処理

  1. stirringAfter stirring an additional 1 hour
  2. customto form a homogeneous solution which
  3. customwas purified by revere phase chromatography
  4. additionThe product containing peaks

出典と根拠

ORDレコード
ord-03e09ac3e43f4c0f969f2329050613e8
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187472B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート