Isopropylamine → HCID 67501040, compound

HRID 1625258Notes

Reaction equation

HRID 1625258 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, compoundYield 36%

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-10c475e853a8438aa326f35c65a19626
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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