Acetone → HCID 11756828, compound

HRID 1782136Notes

Reaction equation

HRID 1782136 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH:16]([C:19]1[N:20]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:21](=[O:29])[C:22]2[C:27]([CH3:28])=[N:26][S:25][C:23]=2[N:24]=1)[CH2:17][CH3:18])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:51][C:52]([CH3:54])=O>C(O)(=O)C>[CH2:30]([N:20]1[C:21](=[O:29])[C:22]2[C:27]([CH3:28])=[N:26][S:25][C:23]=2[N:24]=[C:19]1[CH:16]([N:6]([CH2:5][CH2:4][CH2:3][NH:2][CH:52]([CH3:54])[CH3:51])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[CH2:17][CH3:18])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 54757319HCID 54757319, compound

Product 1

HCID 11756828HCID 11756828, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a solution of N-(3-amino-propyl)-N-[1-(5-benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-propyl]-4-methyl-benzamide hydrogen chloride (method 13g) (1.24 g, 2.54 mmol), in the presence of molecular sieves (2 g,) was added acetone (1 mL) and the mixture was stirred at room temperature for 2 h. Analysis of the reaction mixture by MS showed the completion of the schiff's base formation. To this mixture was added two drops of acetic acid followed by sodium triacetoxyborohydride (220 mg) and the mixture was stirred overnight. The reaction mixture was filtered and the filtrate was washed with water, dried (Na2SO4) and concentrated to get the crude product which was purified by column chromatography (silica gel) using 0-30 % EtOAc in hexanes. N-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isothiazolo[5,4-d]pyrimidin-6-yl)-propyl]-N-(3-isopropylamino-propyl)-4-methyl-benzamide was isolated as a white foam. Yield 0.206 g (15%). m/z 532 (MH+); 1H NMR (DMSO-d6, 96° C.) δ: 0.65 (t, 3H), 1.05 (d, 6H), 1.26-1.48 (m, 1H), 1.65-1.70 (m, 1H), 1.80-1.98 (m, 1H), 2.00-2.17 (m, 1H), 2.35 (s, 3H), 2.63 (b, 2H), 2.80 (s, 3H), 3.05 (b, 1H), 3.40 (t, 2H), 4.90 (d, 1H), 5.50 (bs, 1H), 5.80 (d, 1H), 7.35-7.00 (m, 9H).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto get the crude product which
  7. customwas purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-74d6595daca041fd97c7ce6f78c91b53
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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