Triethylamine → Thieno(3,2-B)pyridine-2-sulfonic acid (1-(1-amino-isoquinolin-7-ylmethyl)-2-oxo-pyrroldin-3-YL)-amide

HRID 394611

Reaction equation

HRID 394611 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][N:15]=[C:16]3Cl)=[CH:11][CH:10]=2)[C:4]1=[O:20].C([N:23](CC)CC)C.[S:28]1[C:36]2[C:31](=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[S:37](Cl)(=[O:39])=[O:38]>CC#N>[NH2:23][C:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([CH2:8][N:5]3[CH2:6][CH2:7][C@H:3]([NH:2][S:37]([C:29]4[S:28][C:36]5[C:31](=[N:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=4)(=[O:39])=[O:38])[C:4]3=[O:20])[CH:18]=2)[CH:13]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18176395Thieno[3,2-b]pyridine-2-sulfonyl chlorideHCID 206807083-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride

Product 1

HCID 445480Thieno(3,2-B)pyridine-2-sulfonic acid (1-(1-amino-isoquinolin-7-ylmethyl)-2-oxo-pyrroldin-3-YL)-amideYield 33.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(S)-amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride (0.15 g, 0.48 mmol) suspended in CH3CN (2.5 mL) is added triethylamine (0.23 mL, 1.6 mmol) followed by thieno[3,2-b]pyridine-2-sulfonyl chloride (0.14 g, 0.55 mmol). The mixture is stirred overnight, then concentrated. The residue is diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to give the title compound (0.076 g, 0.16 mmol) as a light yellow solid.

Workup

  1. concentrationconcentrated
  2. additionThe residue is diluted with CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product is purified by column chromatography
  8. washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-49ab99c121e24c79b203a0490626ddbf
Source dataset
uspto-grants-2003_08
Patent number
US06602864B1

Linked notes

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