Pseudosaccharin chloride → HCID 178490771, compound

HRID 1242090Notes

Reaction equation

HRID 1242090 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4](=[O:12])(=[O:11])[N:3]=1.C(N(C(C)C)CC)(C)C.[C:22]([O:26][C:27]([C:29]1[C:37]2[CH2:36][CH2:35][N:34]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[CH:33]([CH2:47][NH2:48])[C:32]=2[S:31][C:30]=1[NH2:49])=[O:28])([CH3:25])([CH3:24])[CH3:23]>ClCCl>[C:22]([O:26][C:27]([C:29]1[C:37]2[CH2:36][CH2:35][N:34]([CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)[CH:33]([CH2:47][NH:48][C:2]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[S:4](=[O:12])(=[O:11])[N:3]=3)[C:32]=2[S:31][C:30]=1[NH2:49])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 64783Pseudosaccharin chlorideHCID 81531DiisopropylethylamineHCID 219366842-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

Product 1

HCID 178490771HCID 178490771, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Chloro-benzo[d]isothiazole-1,1-dioxide (160 mg, 0.79 mmol) and diisopropylethylamine (1501 μl, 0.86 mmol) were dissolved in dichloromethane (7 ml) at 0° C. 2-Amino-7-aminomethyl-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (284 mg, 0.70 mmol) was added and the mixture was stirred for 15 minutes at 0° C., diluted with dichloromethane, (10 ml) and washed with water (20 ml) and brine (20 ml). The organic phase was dried (MgSO4), filtered, and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of hexanes/ethyl acetate (1:1) to pure ethyl acetate as eluent, which afforded 309 mg (77%) of 2-amino-7-((1,1-dioxo-1H-benzo[d]isothiazol-3-ylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as an foam.

Workup

  1. washwashed with water (20 ml) and brine (20 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5d692e9186ce45a9b5664d2edd5f3eeb
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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