4-(5-Aza-spiro[2.4]hept-5-yl)-5-chloro-benzene-1,2-diamine → HCID 178453056, compound

HRID 1258643Notes

Reaction equation

HRID 1258643 reaction equation
[CH2:1]1[C:3]2([CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[C:10]([NH2:16])[C:11]([NH2:15])=[CH:12][C:13]=3[Cl:14])[CH2:4]2)[CH2:2]1.[C:17]([O:21][C:22](=[O:35])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N:32]=[C:33]=S)[CH:26]=1)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22](=[O:35])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([NH:32][C:33]2[NH:16][C:10]3[CH:9]=[C:8]([N:5]4[CH2:6][CH2:7][C:3]5([CH2:1][CH2:2]5)[CH2:4]4)[C:13]([Cl:14])=[CH:12][C:11]=3[N:15]=2)[CH:26]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 679578314-(5-Aza-spiro[2.4]hept-5-yl)-5-chloro-benzene-1,2-diamineHCID 86646335tert-Butyl 4-chloro-3-isothiocyanatobenzylcarbamate

Product 1

HCID 178453056HCID 178453056, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (130 μL, 0.9 mmol) followed by 4-(5-aza-spiro[2.4]hept-5-yl)-5-chloro-benzene-1,2-diamine (80 mg) were added to (4-chloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester (example 1, step (c), 69 mg, 0.2 mmol) in DMF (3 mL). The reaction mixture was stirred at rt overnight, then concentrated and purified by chromatography to give the sub-title compound.

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography

Sources & evidence

ORD record
ord-61ad8c98291a41f9a5b511f63b4cf353
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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