alpha-Naphthyl isocyanate → HCID 10318790, compound

HRID 457617Notes

Reaction equation

HRID 457617 reaction equation
[C:1]1([N:11]=[C:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C:21]1([C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]1)[CH2:20][CH2:19]2.C(N(CC)C(C)C)(C)C>C1COCC1>[C:1]1([NH:11][C:12]([NH:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH2:22][C:21]2([C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]2)[CH2:20][CH2:19]3)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 66589alpha-Naphthyl isocyanateHCID 81531DiisopropylethylamineHCID 18440311HCID 18440311, compound2×

Product 1

HCID 10318790HCID 10318790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-naphthyl isocyanate (9.5 mg, 0.056 mmol), (±)-6′-amino-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione hydrochloride (described in Intermediate 2) (15 mg, 0.056 mmol), and N,N-diisopropylethylamine (0.010 mL, 0.056 mmol) was stirred in THF (0.5 mL) at ambient temperature for 18 h. The crude mixture was 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=401 (M+1). HRMS: m/z=401.1638; calculated m/z=401.1608 for C23H21N4O3.

Workup

  1. customThe crude mixture was purified by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-cf2871f8ce6c43c797c6ef71fedef90e
Source dataset
uspto-grants-2007_03
Patent number
US07189722B2

Reaction notes

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