Isopropylamine → HCID 67501040, compound

HRID 921570Notes

Reaction equation

HRID 921570 reaction equation
C([C:4]1[C:5]([Cl:36])=[C:6]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH:23]=[C:22]([C:24]5[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=5)[N:21]=[CH:20]4)=[C:13]3[C:12]([CH:33]([CH3:35])[CH3:34])=[N:11]2)[CH:7]=[CH:8][CH:9]=1)(=O)N.Cl.C(N=C=NCCC[N:46]([CH3:48])C)C.[OH2:49].O[C:51]1[C:59]2[N:58]=NN[C:55]=2C=CC=1.C(N)(C)C>CN(C=O)C.O.C(Cl)(Cl)Cl>[C:48]([C:9]1[CH:8]=[CH:7][C:6]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([N:19]4[CH:23]=[C:22]([C:24]5[CH:25]=[CH:26][C:27]([C:28]([NH:58][CH:59]([CH3:55])[CH3:51])=[O:30])=[CH:31][CH:32]=5)[N:21]=[CH:20]4)=[C:13]3[C:12]([CH:33]([CH3:34])[CH3:35])=[N:11]2)=[C:5]([Cl:36])[CH:4]=1)(=[O:49])[NH2:46]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67502587HCID 67502587, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 67501040HCID 67501040, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Compound (150a) (0.07 g), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.035 g), hydroxybenzotriazole monohydrate (0.025 g), and isopropylamine (0.085 mL) were dissolved in DMF (0.6 mL), followed by stirring at room temperature for 3 hr. The reaction solution was distributed between chloroform and water, and the organic layer was washed with saturated saline and was dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (150) (36% as a white solid.

Workup

  1. washthe organic layer was washed with saturated saline
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away
  4. customthe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-17d586e2c89348a0a1382161f46b51a2
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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