Triethylamine → (-) N-{1-[4-(4-cyanotetrahydro-2H-thiopyran-4-yl)-2-methylphenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide

HRID 419999노트

반응식

HRID 419999 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].[NH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:31]#[N:32])[CH2:30][CH2:29][S:28][CH2:27][CH2:26]2)=[CH:21][C:20]=1[CH3:33])[CH3:18].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[C:31]([C:25]1([C:22]2[CH:23]=[CH:24][C:19]([CH:17]([NH:16][C:11](=[O:13])[CH2:10][N:7]3[C:6]4[C:14]([F:15])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[N:9]=[CH:8]3)[CH3:18])=[C:20]([CH3:33])[CH:21]=2)[CH2:26][CH2:27][S:28][CH2:29][CH2:30]1)#[N:32]

참가 물질

5

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 582984404-[4-(1-aminoethyl)-3-methylphenyl]tetrahydro-2H-thiopyran-4-carbonitrile

생성물 1

HCID 24850174(-) N-{1-[4-(4-cyanotetrahydro-2H-thiopyran-4-yl)-2-methylphenyl]ethyl}-2-(6,7-difluoro-1H-benzimidazol-1-yl)acetamide

실험 절차

The amide is synthesized according to example 1 by mixing (6,7-difluoro-1H-benzimidazol-1-yl)acetic acid (96 mg, 0.45 mmol) prepared according to scheme 2, 4-[4-(1-aminoethyl)-3-methylphenyl]tetrahydro-2H-thiopyran-4-carbonitrile (129 mg, 0.50 mmol) prepared according to scheme 14, Et3N (0.69 μL, 0.50 mmol) and HATU (189 mg, 0.50 mmol) in MECN (3.0 mL). The compound is purified by silica gel column chromatography (10% MeOH in DCM) (121 mg, 59%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.35 (d, J=7.03 Hz, 3H), 2.05-2.16 (m, 2H), 2.26-2.35 (m, 5H), 2.72-2.81 (m, J=14.06 Hz, 2H), 2.88-2.99 (m, J=12.50, 12.50 Hz, 2H), 5.01-5.11 (m, 3H), 7.16-7.26 (m, 1H), 7.30 (s, 1H), 7.33-7.38 (m, 1H), 7.39-7.48 (m, 2 H), 8.18 (s, 1H), 8.84 (d, J=7.42 Hz, 1H). MS [M+H], calcd: 455.5. found: 455.3.

후처리

  1. customprepared
  2. customprepared
  3. customThe compound is purified by silica gel column chromatography (10% MeOH in DCM) (121 mg, 59%)

출처 및 근거

ORD 기록
ord-0a44c8d68dc64e659bbb3de4a8f1929e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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