Triethylamine → n-[4-(1-Cyano-1-methylethyl)-3-fluorobenzyl]-2-(6,7-difluoro-1h-benzimidazol-1-yl)acetamide

HRID 419995노트

반응식

HRID 419995 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH2:10][C:11]([OH:13])=O)[C:6]=2[C:14]=1[F:15].Cl.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:29])([CH3:28])[C:26]#[N:27])=[C:21]([F:30])[CH:20]=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>[C:26]([C:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:11](=[O:13])[CH2:10][N:7]2[C:6]3[C:14]([F:15])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[CH:20][C:21]=1[F:30])([CH3:29])[CH3:28])#[N:27]

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 57939018HCID 57939018, 화합물HCID 666493672-[4-(Aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride

생성물 1

HCID 59804254n-[4-(1-Cyano-1-methylethyl)-3-fluorobenzyl]-2-(6,7-difluoro-1h-benzimidazol-1-yl)acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-[4-(1-Cyano-1-methylethyl)-3-fluorobenzyl]-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide is synthesized according to example 14 with (6,7-difluoro-1H-benzimidazol-1-yl)acetic acid (150 mg, 0.707 mmol) prepared according to scheme 2, 2-[4-(aminomethyl)-2-fluorophenyl]-2-methylpropanenitrile hydrochloride (194 mg, 0.848 mmol) prepared according to scheme 8, Et3N (237 μL, 1.70 mmol) and HATU (323 mg, 0.848 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=25 mg as TFA salt, 0.05 mmol, 7%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.74-1.87 (m, 6H), 4.43 (d, J=5.66 Hz, 2H), 5.22 (s, 2H), 7.19-7.40 (m, 2H), 7.45-7.61 (m, 2H), 8.34 (s, 1H), 8.91-9.04 (m, 1H). MS [M+H], calcd: 387.1. found: 387.0.

후처리

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

출처 및 근거

ORD 기록
ord-359b654dc9754100b9a4a17715ebc999
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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