Hydrochloric Acid → HCID 59224707, compound

HRID 1811721Notes

Reaction equation

HRID 1811721 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[C:4]([Cl:14])[N:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:37]([O:41][C:42](=[O:48])[NH:43][CH2:44][CH2:45][CH2:46][NH2:47])([CH3:40])([CH3:39])[CH3:38].C(N(C(C)C)CC)(C)C.Cl>CN(C)C=O>[C:37]([O:41][C:42](=[O:48])[NH:43][CH2:44][CH2:45][CH2:46][NH:47][C:11](=[O:13])[CH2:10][CH2:9][S:8][C:6]1[CH:5]=[C:4]([Cl:14])[N:3]=[C:2]([NH2:1])[N:7]=1)([CH3:40])([CH3:38])[CH3:39]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 59224706HCID 59224706, compound

Product 1

HCID 59224707HCID 59224707, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-Amino-6-chloropyrimidin-4-ylsulfanyl)propionic acid (240 mg) obtained in Step 1 above and N-hydroxybenzotriazole (180 mg, 1.33 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (4.0 ml) was added thereto. 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (255 mg, 1.33 mmol), 3-aminopropylcarbamic acid tert-butyl ester (155 mg, 0.89 mmol), and diisopropylethylamine (0.79 ml, 4.52 mmol) were added to the solution. The resulting mixture was stirred at room temperature for 4 hours. The reaction was stopped with 1N hydrochloric acid, and the solution was extracted with ethyl acetate. The ethyl acetate solution was sequentially washed with 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution. The washed ethyl acetate solution was dried over anhydrous sodium sulfate (10 g). After filtration, the filtrate was concentrated under reduced pressure to yield {3-[3-(2-amino-6-chloropyrimidin-4-ylsulfanyl)propionylamino]propyl}carbamic acid tert-butyl ester (175 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe ethyl acetate solution was sequentially washed with 1N hydrochloric acid
  3. dry with materialThe washed ethyl acetate solution was dried over anhydrous sodium sulfate (10 g)
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cceeaff7f1d489d83127ea87fc52ffa
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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