Triethylamine → 2-(7-Chloro-1h-benzimidazol-1-yl)-n-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide

HRID 419993노트

반응식

HRID 419993 반응식
[Cl:1][C:2]1[C:7]2[N:8]([CH2:11][C:12]([OH:14])=O)[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:28])([CH3:27])[C:25]#[N:26])=[C:20]([F:29])[CH:19]=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[C:7]2[N:8]([CH2:11][C:12]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([C:25]#[N:26])([CH3:28])[CH3:27])=[C:20]([F:29])[CH:19]=3)=[O:14])[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 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 11206606(7-Chloro-1H-benzimidazol-1-yl)acetic acidHCID 666493672-[4-(Aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride

생성물 1

HCID 598042572-(7-Chloro-1h-benzimidazol-1-yl)-n-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(7-Chloro-1H-benzimidazol-1-yl)-N-[4-(1-cyano-1-methylethyl)-3-fluorobenzyl]acetamide is synthesized according to example 14 with (7-chloro-1H-benzimidazol-1-yl)acetic acid (150 mg, 0.712 mmol) prepared according to scheme 1, and 2-[4-(aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride (196 mg, 0.855 mmol) prepared according to scheme 8, Et3N (238 μL, 1.71 mmol) and HATU (325 mg, 0.855 mmol) in DMF (3.0 mL). The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (50 21.2×50 mm, Mobile phase: A=water (0.075% TFA) B=MeCN (0.075% TFA). Yield=14 mg as TFA salt, 0.035 mmol, 5%); 1H NMR (400 MHz, DMSO-D6) δ ppm 1.67 (s, 6H), 4.30 (d, J=5.86 Hz, 2H), 5.24 (s, 2H), 7.10-7.22 (m, 3H), 7.23-7.28 (m, 1H), 7.38 (t, J=8.40 Hz, 1 H), 7.62 (d, J=7.81 Hz, 1H), 8.31 (s, 1H), 8.81 (s, 1H). MS [M+H], calcd: 385.1. found: 385.0.

후처리

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

출처 및 근거

ORD 기록
ord-6214f5543d874bb78be07810d2261836
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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