Triethylamine → 2-(7-Cyano-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyanocyclopropyl)phenyl]ethyl}acetamide

HRID 419986ノート

反応式

HRID 419986 の反応式
[C:1]([C:3]1[C:8]2[N:9]([CH2:12][C:13]([OH:15])=O)[CH:10]=[N:11][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].[NH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[CH3:18].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC#N.O>[C:1]([C:3]1[C:8]2[N:9]([CH2:12][C:13]([NH:16][CH:17]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4([C:28]#[N:29])[CH2:26][CH2:27]4)=[CH:21][CH:20]=3)[CH3:18])=[O:15])[CH:10]=[N:11][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11195002(7-Cyano-1H-benzimidazol-1-yl)acetic acidHCID 582984511-[4-(1-Aminoethyl)phenyl]cyclopropanecarbonitrile

生成物 1

HCID 598042562-(7-Cyano-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyanocyclopropyl)phenyl]ethyl}acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

2-(7-Cyano-1H-benzimidazol-1-yl)-N-{1-[4-(1-cyanocyclopropyl)phenyl]ethyl}acetamide is synthesized according to example 5 by mixing (7-cyano-1H-benzimidazol-1-yl)acetic acid (86.5 mg, 0.430 mmol) prepared according to scheme 3, 1-[4-(1-aminoethyl)phenyl]cyclopropanecarbonitrile (80.0 mg, 0.430 mmol) prepared according to scheme 10, Et3N (131 mg, 1.29 mmol, 0.180 mL) and HATU (163 mg, 0.430 mmol) in MeCN (10.0 mL). The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Synergi Polar (5μ) 21.2×50 mm, Mobile phase: A=water (0.05% TFA) B=MeCN, (23.0 mg, 0.0623 mmol, 14%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.35 (dd, J=7.81, 5.47 Hz, 2H) 1.49 (d, J=7.03 Hz, 3H) 1.68 (dd, J=7.42, 5.08 Hz, 2H) 5.00-5.13 (m, 3H) 6.65 (d, J=7.42 Hz, 1H) 7.22 (d, J=8.59 Hz, 2H) 7.29 (d, J=8.20 Hz, 2H) 7.33 (d, J=7.81 Hz, 1H) 7.59 (d, J=7.62 Hz, 1H) 7.96-8.06 (m, 2H); MS [M+H], calcd: 370.0. found: 370.0.

後処理

  1. customprepared
  2. customprepared
  3. customThe product is purified by HPLC

出典と根拠

ORDレコード
ord-20330f1a67304013bcbcccd7a21663d1
出典データセット
uspto-grants-2012_01
特許番号
US08093402B2

反応ノート

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