Ammonia → HCID 44227708, compound

HRID 1907841Notes

Reaction equation

HRID 1907841 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[C:6]=2[N:7]=1.CCO.[NH3:25]>>[N:18]1[C:19]2[C:14](=[CH:13][C:12]([CH2:11][N:8]3[C:6]4[N:7]=[C:2]([NH2:25])[N:3]=[CH:4][C:5]=4[N:10]=[N:9]3)=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 44227707HCID 44227707, compound

Product 1

HCID 44227708HCID 44227708, compoundYield 90%

Conditions

Temperature
120 °C

Procedure

A suspension of 6-((5-chloro-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)methyl)quinoline (134 mg, 0.453 mmol) in NH3 saturated EtOH (3 mL) was heated at 120° C. in a sealed pressure tube for 2.5 h. After cooling to room temperature, EtOH (20 mL) was added to the reaction mixture. The precipitate was collected by filtration and dried to afford the desired product (112 mg, 90%). 1H NMR (300 MHz, DMSO-d6) δ 5.87 (s, 2H), 7.39 (br s, 2H), 7.51-8.04 (m, 4H), 8.34 (m, 1H), 8.89 (m, 1H), 9.21 (s, 1H); LCMS (APCI) m/z 278.2 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-1fafefe7cf54465198e1a42125b23832
Source dataset
uspto-grants-2013_12
Patent number
US08598184B2

Reaction notes

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