2-Fluoroaniline → HCID 50922689, compound

HRID 1772826Notes

Reaction equation

HRID 1772826 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([N:18]3[CH:22]=[C:21]([C:23]4[C:24]5[CH:31]=[CH:30][NH:29][C:25]=5[N:26]=[CH:27][N:28]=4)[CH:20]=[N:19]3)[CH2:15][C:16]#[N:17])[CH2:10][CH2:9]2)[C:3]=1[CH3:32].[F:33][C:34]1[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=1[NH2:36]>O>[N:26]1[C:25]2[NH:29][CH:30]=[CH:31][C:24]=2[C:23]([C:21]2[CH:20]=[N:19][N:18]([CH:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:4]4[C:3]([CH3:32])=[C:2]([NH:36][C:35]5[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=5[F:33])[N:7]=[CH:6][N:5]=4)[CH2:9][CH2:10]3)[CH2:15][C:16]#[N:17])[CH:22]=2)=[N:28][CH:27]=1

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 58180905HCID 58180905, compound

Product 1

HCID 50922689HCID 50922689, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-[1-(6-chloro-5-methylpyrimidin-4-yl)piperidin-4-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.010 g, 0.022 mmol from step 3 in example 146) and 3 mg TSA.H2O in 2-fluoro-aniline (95 microL, 1.0 mmol) was heated at 160° C. for 1.7 hours. The reaction was purified by preparative-LCMS (pH 10) to give 3.2 mg white solid (50% yield). 1H NMR (400 MHz, DMSO): δ 12.07 (1H, s); 8.78 (1H, s); 8.61 (1H s); 8.37 (1H, s); 8.02 (1H, s); 7.99 (1H, s); 7.55 (1H, d); 7.38 (1H, m); 7.1.5 (1H, m); 7.06 (2H, m); 6.95 (1H, s); 4.57 (1H, m); 3.61 (1H, m); 3.45 (1H, m); 3.27 (2H, m); 2.7 (1H, m); 2.58 (1H, m); 2.02 (1H, m); 1.98 (3H, s); 1.82 (1H, m); 1.3 (2H, m); (1.01 (1H, m). LCMS (M+1): 523.

Workup

  1. customThe reaction was purified by preparative-LCMS (pH 10)

Sources & evidence

ORD record
ord-47c96b289b4d4224a5dbe0da89b0d783
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

Loading…