HCID 66611452, compound → HCID 59548264, compound

HRID 1812045Notes

Reaction equation

HRID 1812045 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[N:18]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 1

HCID 66611452HCID 66611452, compound

Product 1

HCID 59548264HCID 59548264, compoundYield 24.03%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2-(5-chloro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (0.3068 g, 0.525 mmol) in TFA (8.0 mL) (Aldrich) was heated at 80° C. overnight. The solution was cooled to room temperature, and concentrated to about 50% of the original volume. The remaining mixture was pipetted carefully into a saturated solution of NaHCO3, which had been cooled in an ice bath. The resulting precipitate was removed by filtration and washed with water. The solid was dissolved in DCM and MeOH, and dry packed with silica gel. Purification using an ISCO Combiflash Companion (12 g column, 1-6% MeOH in DCM over 40 min, product eluted with 4% MeOH) gave 4-(2-(5-chloro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.0434 g, 0.126 mmol, 24.03% yield) as a tan amorphous solid. 1H NMR (400 MHz, d6-DMSO) δ 11.89 (s, 1H); 8.80 (dd, J=7.8, 2.0 Hz, 1H); 8.51-8.56 (m, 2H); 8.35 (dd, J=4.7, 2.0 Hz, 1H); 7.92 (br. s., 1H); 7.76 (br. s., 1H); 6.94 (dd, J=7.8, 4.7 Hz, 1H); 3.93 (s, 3H); 2.43 (s, 3H). m/z (ESI, +ve ion) 344.0 (M+H)+.

Workup

  1. concentrationconcentrated to about 50% of the original volume
  2. temperaturehad been cooled in an ice bath
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. dissolutionThe solid was dissolved in DCM
  6. dry with materialMeOH, and dry
  7. customPurification
  8. washan ISCO Combiflash Companion (12 g column, 1-6% MeOH in DCM over 40 min, product eluted with 4% MeOH)

Sources & evidence

ORD record
ord-054a8635360a473e9caf01154069453a
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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