1-Naphthalenemethanamine → HCID 22337645, compound

HRID 586067Notes

Reaction equation

HRID 586067 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.O=C1CCC(=O)N1[O:29][C:30]([NH:32][C:33]1[CH:41]=[CH:40][CH:39]=[C:38]2[C:34]=1[CH:35]=[N:36][N:37]2[C:42]([O:44][CH3:45])=[O:43])=O>CN(C=O)C.O>[C:1]1([CH2:11][NH:12][C:30]([NH:32][C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[N:36][N:37]3[C:42]([O:44][CH3:45])=[O:43])=[O:29])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 81531DiisopropylethylamineHCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

Product 1

HCID 22337645HCID 22337645, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Naphthylmethylamine (2.1 mmol) and diisopropylethylamine (2 mmol, 0.26 g) were combined in DMF (6 mL) and treated with methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate (6.6 g, 2 mmol) at ambient temperature. After stirring for 30 minutes, the reaction mixture was diluted with water (6 ml) and filtered. The filter cake was washed with water:acetonitrile (1:1) and dried to provide the title compound. 1H NMR (DMSO-d6) δ 4.02 (s, 3H); 4.81 (d, 2H); 6.85 (m, 1H); 7.42-7.64 (m, 5H); 7.67 (d, 1H); 7.87 (m, 2H); 7.97 (d, 1H); 8.15 (d, 1H); 8.38 (s, 1H); 8.99 (s, 1H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water:acetonitrile (1:1)
  3. customdried

Sources & evidence

ORD record
ord-be5f2794584e4572be5c7d210c1e5450
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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