Diisopropylethylamine → HCID 85469417, compound

HRID 531218Notes

Reaction equation

HRID 531218 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:31])[NH:6]2.OC1[C:41]2[N:40]=NN[C:37]=2[CH:36]=[CH:35][CH:34]=1.C(O)(=O)C(O)=O.[CH2:48]1C2(CCNCC2)[CH2:50][O:49]1.C1C2(CCNCC2)CO1.C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24][CH2:25][CH2:26][CH2:27][C:28]([N:40]4[CH2:34][CH2:35][C:36]5([CH2:50][O:49][CH2:48]5)[CH2:37][CH2:41]4)=[O:29])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:31])[NH:6]2

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 714636191379811-94-5HCID 86730385HCID 86730385, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 85469417HCID 85469417, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 8 (9.8 g, crude, containing lithium chloride) in N,N-dimethylformamide (100 mL) was added hydroxybenzotriazole (6.22 g, 46.07 mmol), 2-oxa-7-azaspiro[3.5]nonan hemioxalate (4.39 g, 34.56 mmol), N,N-diisopropylethylamine (8.93 g, 69.11 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.83 g, 46.07 mmol) sequentially. The reaction mixture was stirred overnight at room temperature and then poured into water (800 mL). Gray solid formed was collected by filtration. This solid was purified by flash chromatography (gradient from dichloromethane to dichloromethane:methanol 10:1) to give Compound 9 (5.20 g) as an off-white solid. m/z 535.3 (M+H, 100%) (positive ionization mode). 1H-NMR (CDCl3, 400 MHz): δ 1.83 (4H, m); 2.27 (2H, m); 2.30 (3H, s); 2.46 (2H, t); 3.41 (2H, t); 3.42 (2H, t); 4.05 (3H, s); 4.27 (2H, t); 4.46 (4H, q); 6.34 (1H, q); 7.0 (1H, dd); 7.10 (1H, d); 7.34 (1H, s); 7.63 (1H, s); 8.17 (1H, s); 8.60 (1H, s).

Workup

  1. customGray solid formed
  2. filtrationwas collected by filtration
  3. customThis solid was purified by flash chromatography (gradient from dichloromethane to dichloromethane:methanol 10:1)

Sources & evidence

ORD record
ord-c0ad81ddb9044397ba6647b0fc9eccb4
Source dataset
uspto-grants-2016_05
Patent number
US09353123B2

Reaction notes

Loading…