Hydrochloric Acid → HCID 22063508, compound

HRID 1828452Notes

Reaction equation

HRID 1828452 reaction equation
COC1C=CC(C[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]([OH:26])=O)=[CH:23][C:16]4=[N:15][CH:14]=3)=[N:9]2)=CC=1.[C:29]([C:33]1[N:34]=[C:35]([NH2:38])[S:36][CH:37]=1)([CH3:32])([CH3:31])[CH3:30].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:29]([C:33]1[N:34]=[C:35]([NH:38][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][NH:8][N:9]=4)=[CH:14][N:15]=[C:16]3[CH:23]=2)=[O:26])[S:36][CH:37]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27342024-tert-Butyl-1,3-thiazol-2-amineHCID 22063552HCID 22063552, compound

Product 1

HCID 22063508HCID 22063508, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

3-[2-(4-Methoxybenzyl)-2H-1,2,3,4-tetrazol-5-yl]-4-oxo-4H-pyrido[1,2-a]-pyrimidine-8-carboxylic acid (40 mg, 0.114 mmol) was added with dimethylformamide (2 ml), 4-(tert-butyl)-1,3-thiazol-2-amine (20 mg, 0.125 mmol), 1-hydroxybenzotriazole (20 mg, 0.136 mmol) and 4-dimethylaminopyridine (21 mg, 0.170 mmol) at room temperature, then added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (35 mg, 0.170 mmol) at room temperature, and stirred at room temperature for 24 hours. The reaction solution was added dropwise with 1 N hydrochloric acid (3 ml) at room temperature, and the deposited yellow crystals were taken by filtration and washed with water. The crystals were dissolved in chloroform and ethanol, concentrated under reduced pressure, and dried to obtain the title compound as yellow crystals without purification. The product was dissolved in anisole (0.2 ml) and trifluoroacetic acid (5 ml), stirred at room temperature for 5 hours, and added with water. The deposited yellow crystals were collected by filtration and washed with water, and the resulting crystals were dissolved in chloroform and ethanol and concentrated under reduced pressure. The crude crystals was added with ethanol, taken by filtration and washed with diethyl ether to obtain 28 mg (67% for the two steps) of the title compound as yellow crystals.

Workup

  1. filtrationthe deposited yellow crystals were taken by filtration
  2. washwashed with water
  3. dissolutionThe crystals were dissolved in chloroform
  4. concentrationethanol, concentrated under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-20ceb9e64c5643ecbb4e59740beb7a0f
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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