Isopropylamine → HCID 59525932, compound

HRID 385822Notes

Reaction equation

HRID 385822 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.O[N:38]1[C:42]2[CH:43]=CC=C[C:41]=2N=N1.C(N)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[CH2:12][C:13]([NH:38][CH:42]([CH3:43])[CH3:41])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59526017HCID 59526017, compound

Product 1

HCID 59525932HCID 59525932, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[(Benzyloxy)carbonyl]-N-[(6-bromopyridin-2-yl)methyl]glycine (0.16 g, 0.42 mmol) was dissolved in DMF (2.1 mL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.081 g, 0.42 mmol) and 1-hydroxybenzotriazole hydrate (0.066 g, 0.43 mmol) were added. Isopropyl amine (0.025 g, 0.42 mmol) was added and the reaction was stirred overnight. The reaction was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to yield the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier)

Sources & evidence

ORD record
ord-2313722aadab4a49a7b2b1ca9f3ce83d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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