3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline → HCID 44193277, compound

HRID 1855435Notes

Reaction equation

HRID 1855435 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Cl[C:17]1[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]2)[CH:20]=[C:19]([CH3:30])[N:18]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]2[N:22]=[C:21]([N:23]3[CH2:24][CH2:25][CH:26]([OH:29])[CH2:27][CH2:28]3)[CH:20]=[C:19]([CH3:30])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

3

Reactant 2

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 60137850HCID 60137850, compound

Product 1

HCID 44193277HCID 44193277, compoundYield 82%

Procedure

The title compound was prepared from 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (41 mg, 0.20 mmol) and 1-(2-chloro-6-methyl-pyrimidin-4-yl)-piperidin-4-ol (50 mg, 0.22 mmol) in analogous manner as described in example 90. It was obtained in 82% yield as a light brown solid. MS ISP (m/e): 395.2 (100) [(M+H)+]; 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.23 (s, 1H), 7.96 (s, 1H), 7.63 (s, 1H), 7.18 (m, 2H), 7.01 (s, 1H), 6.22 (s, 1H), 4.75 (d, 1H), 4.03 (br m, 2H), 3.78 (s, 3H), 3.75 (m, 1H), 3.23 (m, 2H), 2.20 (s, 3H), 2.14 (s, 3H), 1.76 (m, 2H), 1.32 (m, 2H).

Workup

  1. customIt was obtained in 82% yield as a light brown solid

Sources & evidence

ORD record
ord-cd8e039bd7154c47bf845865ab0f6625
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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