Ammonia → HCID 16035377, compound

HRID 2234191Notes

Reaction equation

HRID 2234191 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:28])[CH2:9][CH2:10][N:11]([CH2:25][CH2:26]O)[C:12](=[O:24])[CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[NH2:30][CH2:31][CH2:32][C:33]1[C:41]2[S:40][C:39](=[O:42])[NH:38][C:37]=2[C:36]([OH:43])=[CH:35][CH:34]=1.C([BH3-])#N.[Na+].N>ClCCl.CO.O.C(O)(=O)C.C(N(CC)CC)C.CS(C)=O>[CH3:7][N:8]([CH3:28])[CH2:9][CH2:10][N:11]([CH2:25][CH2:26][NH:30][CH2:31][CH2:32][C:33]1[C:41]2[S:40][C:39](=[O:42])[NH:38][C:37]=2[C:36]([OH:43])=[CH:35][CH:34]=1)[C:12](=[O:24])[CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

12

Reactant 5

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 602075534-Hydroxy-7-(2-aminoethyl)-1,3-benzothiazol-2(3H)-one hydrochlorideHCID 68701705HCID 68701705, compound

Product 1

HCID 16035377HCID 16035377, compound

Reagents, catalysts & solvents 6

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

A solution of dimethyl sulfoxide (0.037 g) in dichloromethane (1 mL) was added to a solution of oxalyl chloride (0.030 g) in dichloromethane (10 mL) at −78° C. The reaction was stirred for 15 minutes and then a solution of N-(2-dimethylaminoethyl)-N-(2-hydroxyethyl)-3-phenethyloxy-propanamide (Example 14a), 0.067 g) in dichloromethane (1 mL+1 mL wash) was added and the reaction stirred for a further 15 minutes. Triethylamine (0.11 g) was added and the reaction mixture was allowed to warm to room temperature over a period of 1 hour. The mixture was subsequently diluted (dichloromethane, 30 mL), the organics washed with saturated sodium hydrogencarbonate solution (20 mL) and then brine (20 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give a crude aldehyde product which was used immediately. The crude product was dissolved in methanol (10 mL) and 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.054 g) added along with acetic acid (0.1 mL) and water (0.1 mL). After stirring at room temperature for 30 minutes, sodium cyanoborohydride (0.014 g) was added and the reaction mixture was stirred overnight. Ammonia (7N in methanol, 1 mL) was added and the mixture was concentrated. The crude residue was purified by flash silica column chromatography eluting with 1% ammonia; 5%-7% methanol in dichloromethane to afford the titled compound as a white solid (0.012 g).

Workup

  1. stirringthe reaction stirred for a further 15 minutes
  2. washthe organics washed with saturated sodium hydrogencarbonate solution (20 mL)
  3. dry with materialbrine (20 mL), dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude aldehyde product which
  7. stirringAfter stirring at room temperature for 30 minutes
  8. stirringthe reaction mixture was stirred overnight
  9. concentrationthe mixture was concentrated
  10. customThe crude residue was purified by flash silica column chromatography
  11. washeluting with 1% ammonia

Sources & evidence

ORD record
ord-c297d500c9c947b68757d4ce9bff17e2
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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