Pyridine → 4-isopropyl-6-(4-(1-methyl-1H-indol-5-yl)-5-(quinolin-6-ylamino)-4H-1,2,4-triazol-3-yl)benzene-1,3-diol

HRID 76110Notes

Reaction equation

HRID 76110 reaction equation
[CH:1]([C:4]1[C:5]([O:38]C)=[CH:6][C:7]([O:36]C)=[C:8]([C:10]2[N:11]([C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[CH:30]=[CH:29]4)[C:12]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].N1C=CC=CC=1>C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:11]([C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[CH:30]=[CH:29]4)[C:12]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[C:7]([OH:36])=[CH:6][C:5]=1[OH:38])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 66986842N-(5-(5-isopropyl-2,4-dimethoxyphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)quinolin-6-amine

Product 1

HCID 1359718874-isopropyl-6-(4-(1-methyl-1H-indol-5-yl)-5-(quinolin-6-ylamino)-4H-1,2,4-triazol-3-yl)benzene-1,3-diolYield 38.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

A tube was charged with N-(5-(5-isopropyl-2,4-dimethoxyphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)quinolin-6-amine (114 mg) and pyridine*HCl (4 g.), and placed under a nitrogen atmosphere. It was heated to 210° C. for 50 minutes, and then cooled. The solid was dissolved in ethyl acetate (20 mL) and washed with a saturated solution of ammonium chloride (3×20 mL). The organic layer was dried and evaporated to give 4-isopropyl-6-(4-(1-methyl-1H-indol-5-yl)-5-(quinolin-6-ylamino)-4H-1,2,4-triazol-3-yl)benzene-1,3-diol (42 mg). In some cases column chromatography was necessary for purification. 1H-NMR (CDCl3): 8.69 (dd, 1H); 8.50 (d, 1H), 8.22 (d, 1H), 7.98 (d, 1H), 7.75 (d, 1H), 7.63 (d, 1H), 7.45-7.36 (m, 2H), 7.33 (d, 1H), 7.27 (dd, 1H), 6.64 (d, 1H), 6.42 (s, 1H), 6.30 (s, 1H), 3.98 (s, 3H); 2.83 (q, 1H); 0.50 (m, 6H). MS: expected ion=491.4; observed ion=491.

Workup

  1. temperaturecooled
  2. washwashed with a saturated solution of ammonium chloride (3×20 mL)
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-5ec4183d4ba343919e66fc4b6ae31dd9
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

Loading…