Hydrochloric Acid → HCID 22063527, compound

HRID 1828456Notes

Reaction equation

HRID 1828456 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[N:12]=[N:11][C:10]([C:13]3[C:18](=[O:19])[N:17]4[CH:20]=[CH:21][C:22]([C:24](O)=[O:25])=[CH:23][C:16]4=[N:15][CH:14]=3)=[N:9]2)=[CH:5][CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Br.[CH:42]([C:45]1[N:46]=[C:47]([NH2:50])[S:48][CH:49]=1)([CH3:44])[CH3:43].Cl>CN(C)C=O>[CH:42]([C:45]1[N:46]=[C:47]([NH:50][C:24]([C:22]2[CH:21]=[CH:20][N:17]3[C:18](=[O:19])[C:13]([C:10]4[N:11]=[N:12][N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=5)[N:9]=4)=[CH:14][N:15]=[C:16]3[CH:23]=2)=[O:25])[S:48][CH:49]=1)([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-Carbonyldiimidazole3×HCID 12696971HCID 12696971, compoundHCID 22063552HCID 22063552, compound

Product 1

HCID 22063527HCID 22063527, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-[2-(4-Methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-4-oxo-4H-pyrido[1,2-a]-pyrimidine-8-carboxylic acid (250 mg, 0.66 mmol) was dissolved in dimethylformamide (6 ml), added with N,N-carbonylbis-1H-imidazole (abbreviated as “CDI” hereinafter, 160 mg, 0.991 mmol) and heated to 90° C. with stirring. After 1 hour and 30 minutes, the reaction solution was further added with CDI (170 mg), further stirred for 1 hour, and then further added with CDI (170 mg). The reaction solution was stirred further 2 hours, then returned to room temperature, added with 4-isopropyl-1,3-thiazol-2-amine hydrobromide (1.32 mmol) and stirred at room temperature for 2 hours and 30 minutes. The reaction solution was added with 2 N hydrochloric acid (7 ml), and the deposited crystals were collected by filtration and washed with water. The resulting yellow crystals were dissolved in chloroform and washed with saturated brine, and the collected organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain the title compound as yellow crystals without purification.

Workup

  1. stirringfurther stirred for 1 hour
  2. stirringThe reaction solution was stirred further 2 hours
  3. customreturned to room temperature
  4. stirringstirred at room temperature for 2 hours and 30 minutes
  5. filtrationthe deposited crystals were collected by filtration
  6. washwashed with water
  7. dissolutionThe resulting yellow crystals were dissolved in chloroform
  8. washwashed with saturated brine
  9. dry with materialthe collected organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30da1b4ad96a40fdbe96938ad40121ec
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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