2-Methylquinolin-6-amine → HCID 66611496, compound

HRID 1621628Notes

Reaction equation

HRID 1621628 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:12])[CH:8]=2)[N:3]=1.F[C:14]1[C:19]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([N:27]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[N:21]=2)=[CH:18][CH:17]=[CH:16][N:15]=1>>[CH3:45][O:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][N:27]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[C:22]2[N:23]=[C:24]([CH3:26])[N:25]=[C:20]([C:19]3[C:14]([NH:12][C:7]4[CH:8]=[C:9]5[C:4](=[CH:5][CH:6]=4)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]5)=[N:15][CH:16]=[CH:17][CH:18]=3)[N:21]=2)=[CH:43][CH:42]=1

Participants

3

Reactant 2

HCID 1031482-Methylquinolin-6-amineHCID 595482404-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66611496HCID 66611496, compoundYield 49.1%

Procedure

The title compound was prepared in an analogous manner to that described in Example 164 using 2-methylquinolin-6-amine (Acros Organics) and 4-(2-fluoropyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine. Purification using an ISCO Combiflash Companion (12 g column, 20-60% EtOAc in hexanes over 30 min, product eluted with 35-45% EtOAc) gave the title compound as a yellow amorphous solid (49.1%). 1H NMR (400 MHz, d6-DMSO) δ 12.19 (s, 1H); 8.84 (dd, J=7.8, 2.0 Hz, 1H); 8.45 (dd, J=4.7, 2.0 Hz, 1H); 8.39 (d, J=2.2 Hz, 1H); 8.08 (d, J=8.2 Hz, 1H); 7.78-7.83 (m, 1H); 7.71-7.77 (m, 1H); 7.34 (d, J=8.4 Hz, 1H); 7.26 (dd, J=8.6, 6.3 Hz, 4H); 6.98 (dd, J=7.8, 4.7 Hz, 1H); 6.90 (t, J=8.3 Hz, 4H); 4.84 (d, J=17.6 Hz, 4H); 3.72 (d, J=14.5 Hz, 6H); 2.62 (d, J=2.0 Hz, 6H). m/z (ESI, +ve ion) 584.0 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that
  2. customPurification
  3. washan ISCO Combiflash Companion (12 g column, 20-60% EtOAc in hexanes over 30 min, product eluted with 35-45% EtOAc)

Sources & evidence

ORD record
ord-5d551fb625ca47118f6541fd115b4169
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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