Water → Thieno[3,2-b]pyridine-2-sulfonic acid[1-(1-aminoisoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(r)-yl]amide trifluoroacetate

HRID 651689Notes

Reaction equation

HRID 651689 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[CH:20][N:21]=[C:22]3[NH2:25])=[CH:17][CH:16]=2)[C:10]1=[O:26].C(N(C(C)C)CC)(C)C.[S:36]1[C:44]2[C:39](=[N:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]1[S:45](Cl)(=[O:47])=[O:46].O>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:25][C:22]1[C:23]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:14][N:11]3[CH2:12][CH2:13][C@@H:9]([NH:8][S:45]([C:37]4[S:36][C:44]5[C:39](=[N:40][CH:41]=[CH:42][CH:43]=5)[CH:38]=4)(=[O:46])=[O:47])[C:10]3=[O:26])[CH:24]=2)[CH:19]=[CH:20][N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 18176395Thieno[3,2-b]pyridine-2-sulfonyl chlorideHCID 206806933-(R)-Amino-1-(1-aminoisoquinolin-7-ylmethyl)pyrrolidin-2-one trifluoroacetate

Product 1

HCID 70122297Thieno[3,2-b]pyridine-2-sulfonic acid[1-(1-aminoisoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(r)-yl]amide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-(R)-Amino-1-(1-aminoisoquinolin-7-ylmethyl)pyrrolidin-2-one trifluoroacetate (80 mg, 0.216 mmol) and diisopropylethylamine (140 mg, 1.08 mmol) are dissolved in acetonitrile (12 mL), and stirred at room temperature for 15 minutes before adding thieno[3,2-b]pyridine-2-sulfonyl chloride dropwise as a solution in acetonitrile (8 mL). The reaction mixture is left at room temperature overnight, water (4 mL) added, and the solution concentrated in vacuo to remove the acetonitrile (ca. 4 mL of solution). 75% Acetonitrile/water (4 mL) is added. and the product purified by reverse phase preparative HPLC with gradient elution 10-40% acetonitrile/water (0.1% trifluoroacetic acid). The product fractions are combined, the acetonitrile removed in vacuo, and the aqueous solution lyophilized to give the product as a white powder (52 mg, 0.092 mmol).

Workup

  1. waitThe reaction mixture is left at room temperature overnight
  2. concentrationthe solution concentrated in vacuo
  3. customto remove the acetonitrile (ca. 4 mL of solution)
  4. addition75% Acetonitrile/water (4 mL) is added
  5. customand the product purified by reverse phase preparative HPLC with gradient elution 10-40% acetonitrile/water (0.1% trifluoroacetic acid)
  6. customthe acetonitrile removed in vacuo

Sources & evidence

ORD record
ord-1243990493874caea15c1fba693adeab
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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