5-Fluoro-6-methoxypyridin-3-amine → HCID 66611960, compound

HRID 1621636Notes

Reaction equation

HRID 1621636 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].F[C:12]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:15]=[CH:14][C:13]=1[C:24]1[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[N:25]=1>>[CH3:49][O:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][N:31]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)[C:26]2[N:27]=[C:28]([CH3:30])[N:29]=[C:24]([C:13]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[N:17][C:12]=3[NH:10][C:4]3[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=3)[N:25]=2)=[CH:47][CH:46]=1

Participants

3

Reactant 2

HCID 454803515-Fluoro-6-methoxypyridin-3-amineHCID 66611584HCID 66611584, compound

Product 1

HCID 66611960HCID 66611960, compoundYield 39.6%

Procedure

The title compound was prepared in an analogous manner to that described in Example 164 using 5-fluoro-6-methoxypyridin-3-amine (Anichem) and 4-(6-fluoro-2,4′-bipyridin-5-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine. Purification using an ISCO Combiflash Companion (12 g column and sample loader, 30-100% EtOAc in hexanes over 20 min; the product eluted with 82% EtOAc) afforded the title compound as a brown oil (39.6%). 1H NMR (400 MHz, d6-DMSO) δ 11.86 (s, 1H); 8.91 (d, J=8.2 Hz, 1H); 8.70-8.76 (m, 2H); 8.21 (d, J=2.2 Hz, 1H); 8.09 (dd, J=12.4, 2.2 Hz, 1H); 7.94-7.99 (m, 2H); 7.66 (d, J=8.0 Hz, 1H); 7.26 (dd, J=18.4, 8.6 Hz, 4H); 6.89 (dd, J=18.7, 8.7 Hz, 4H); 4.83 (d, J=9.2 Hz, 4H); 3.95 (s, 3H); 3.74 (s, 3H); 3.70 (s, 3H); 2.59 (s, 3H). m/z (ESI, +ve ion) 645.0 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that
  2. customPurification
  3. customover 20 min
  4. washthe product eluted with 82% EtOAc)

Sources & evidence

ORD record
ord-83ef7ed7e0d24bdba5377cbe1d3bba17
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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