Triethylamine → HCID 59581280, compound

HRID 386613Notes

Reaction equation

HRID 386613 reaction equation
[CH3:1][N:2]1[C@@:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16](=[O:30])[CH2:17][NH:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:21]=4)[CH:12]=3)[CH2:7]2)[C:5](=[O:31])[NH:4][C:3]1=[O:32].[Cl:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36](Cl)=[O:37].C(N(CC)CC)C>C(Cl)Cl>[Cl:33][CH2:34][C:35]([CH3:40])([CH3:39])[C:36]([N:18]([CH2:17][C:16]([NH:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@:6]1([C:5](=[O:31])[NH:4][C:3](=[O:32])[N:2]1[CH3:1])[CH2:14]2)=[O:30])[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 59581353HCID 59581353, compound

Product 1

HCID 59581280HCID 59581280, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[(4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-inden]-5′-yl]-2-[(2-naphthylmethyl)amino]acetamide from Step C (19 mg, 0.044 mmol), in DCM (1 mL), at 0° C. was added 3-chloro-2,2-dimethylpropanoyl chloride (10 mg, 0.067 mmol) and triethylamine (9.0 mg, 0.089 mmol). After 1 hour the reaction mixture was applied directly to a silica gel column for purification, eluting with DCM:MeOH—99:1 to 96:4. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=547 (M(35Cl)+1). HRMS: m/z=547.2103; calculated m/z=547.2107 for C30H32N4O5(35Cl)1.

Workup

  1. customAfter 1 hour the reaction mixture was applied directly to a silica gel column for purification
  2. washeluting with DCM
  3. additionProduct containing fractions
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e85bd8c12ab4f50860fa741d444b611
Source dataset
uspto-grants-2013_02
Patent number
US08372859B2

Reaction notes

Loading…