Triethylamine → HCID 10364027, compound

HRID 457618Notes

Reaction equation

HRID 457618 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]1)[CH2:5]2.[C:17]1([S:27](Cl)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1COCC1>[C:17]1([S:27]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C:6]2([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]2)[CH2:5]3)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chlorideHCID 184403095'-Amino-1',3'-dihydro-2H,5H-spiro[imidazolidine-4,2'-indene]-2,5-dione2×

Product 1

HCID 10364027HCID 10364027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 50 mg (0.23 mmol) (±)-5′-amino-spiro[imidazolidine-4,2′-indane]-2,5-dione (described in Intermediate 6) in THF (3 mL) was added 1-naphthalenesulfonyl chloride (53 mg, 0.24 mmol) and triethylamine (0.034 mL, 0.24 mmol). After 30 min the reaction mixture was concentrated to dryness. The residue was dissolved in DMF and purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound as a white solid. MS: m/z=408 (M+1). HRMS: m/z=408.1019; calculated m/z=408.1013 for C21H17N3O4S.

Workup

  1. concentrationAfter 30 min the reaction mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in DMF
  3. custompurified by HPLC
  4. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-07f37e41f9084bcdbc87a4319ccff64b
Source dataset
uspto-grants-2007_03
Patent number
US07189722B2

Reaction notes

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