Isopropylamine → 2-N-Methyl-2-N-phenyl-6-(5-{6-[(propan-2-yl)amino]pyridin-3-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamine

HRID 341444Notes

Reaction equation

HRID 341444 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]3[N:18]=[C:17]([N:19]([CH3:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:15]([NH2:27])[N:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH:28]([NH2:31])([CH3:30])[CH3:29].CCN(C(C)C)C(C)C>CCO>[CH3:26][N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17]1[N:16]=[C:15]([NH2:27])[N:14]=[C:13]([C:10]2[N:9]=[C:8]([C:5]3[CH:6]=[N:7][C:2]([NH:31][CH:28]([CH3:30])[CH3:29])=[CH:3][CH:4]=3)[O:12][N:11]=2)[N:18]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 867105136-[5-(6-chloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamine2×

Product 1

HCID 668034262-N-Methyl-2-N-phenyl-6-(5-{6-[(propan-2-yl)amino]pyridin-3-yl}-1,2,4-oxadiazol-3-yl)-1,3,5-triazine-2,4-diamineYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-[5-(6-chloropyridin-3-yl)-1,2,4-oxadiazol-3-yl]-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamine (Intermediate 135, 0.100 g, 0.263 mmol), isopropylamine (0.087 mL, 1.052 mmol), DIPEA (0.091 mL, 0.525 mmol) in EtOH (1 mL) was heated 3 times under microwave conditions (first treatment: 100 W, 130 C, 40 min; second treatment: 100 W, 130 C, 45 min; third treatment: 100W, 130 C, 45 min). The reaction mixture was cooled down and concentrated under vacuum. The resulting dark oil was purified by preparative HPLC, to afford the title compound (29 mg, 27%).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. concentrationconcentrated under vacuum
  3. customThe resulting dark oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-1de61bba695742539dc7615916b3ef16
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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