Diisopropylethylamine → HCID 22591779, compound

HRID 22903Notes

Reaction equation

HRID 22903 reaction equation
Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.Cl.[NH2:24][CH:25]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(N(CC)C(C)C)(C)C.[O:47]=[C:48]1[N:52]([C:53]2[CH:58]=[CH:57][CH:56]=[C:55]([NH:59][C:60]([NH:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[O:61])[CH:54]=2)[CH2:51][CH:50]([C:70](O)=[O:71])[CH2:49]1>CN(C)C=O>[F:37][C:33]1[CH:32]=[C:31]([CH:25]([NH:24][C:70]([CH:50]2[CH2:49][C:48](=[O:47])[N:52]([C:53]3[CH:58]=[CH:57][CH:56]=[C:55]([NH:59][C:60]([NH:62][CH2:63][C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=4)=[O:61])[CH:54]=3)[CH2:51]2)=[O:71])[CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22591791HCID 22591791, compoundHCID 22591793HCID 22591793, compound

Product 1

HCID 22591779HCID 22591779, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

1-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (99.5 mg, 0.52 mmol, 1.2 equiv), 1-hydroxy-7-azabenzotriazole (12.2 mg, 0.090 mmol, 0.2 equiv), methyl 3-amino-3-(3-fluorophenyl)propanoate hydrochloride (118.8 mg, 0.51 mmol, 1.2 equiv), and N,N-diisopropylethylamine (0.18 mL, 1.03 mmol, 2.4 equiv) were added sequentially to a solution of 5-oxo-1-(3-{(benzylamino)carbonylamino}phenyl)pyrrolidine-3-carboxylic acid (152.2 mg, 0.43 mmol, 1 equiv) in N,N-dimethylformamide (3.0 mL). The resulting solution was stirred at 23° C. for 92 hr. The reaction was partitioned between an aqueous solution of hydrochloric acid (1.5 N, 20 mL) and ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate, were filtered, and were concentrated in vacuo. The residue was purified by flash column chromatography (90% ethyl acetate in hexanes) to give two diastereomers of the title compound (first diastereomer and second diastereomer) as white solids.

Workup

  1. customThe reaction was partitioned between an aqueous solution of hydrochloric acid (1.5 N, 20 mL) and ethyl acetate (3×25 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationwere filtered
  4. concentrationwere concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a673c017c9a444cdb9343e55c7eb3a9f
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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