Propylamine → HCID 86714116, compound

HRID 919788Notes

Reaction equation

HRID 919788 reaction equation
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:15]([C:19]#[N:20])=[N:14][C:13]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=O)=[O:22])=[C:12]([OH:30])[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:46]([NH2:49])[CH2:47][CH3:48]>C(Cl)Cl>[CH2:46]([NH:49][C:27]([CH2:26][CH2:25][CH2:24][NH:23][C:21]([C:13]1[N:14]=[C:15]([C:19]#[N:20])[C:16]2[C:17](=[O:18])[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:9]=[CH:10][C:11]=2[C:12]=1[OH:30])=[O:22])=[O:29])[CH2:47][CH3:48]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 68297177HCID 68297177, compound

Product 1

HCID 86714116HCID 86714116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[(7-benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carbonyl)-amino]-butyric acid (30 mg, 0.074 mmol) and triethylamine (0.015 mL, 0.11 mmol) in CH2Cl2 (3 mL) was cooled in an ice bath. Isobutyl chloroformate (0.014 mL, 0.11 mmol) was added, and the mixture was stirred at 0° C. for 10 min. Propylamine (0.1 mL) was then added, and the mixture was slowly warmed to r.t. and stirred for 16 h. The mixture was diluted with CH2Cl2 (30 mL) and washed with 1 M HCl. The organic layer was dried over MgSO4 and concentrated. The crude product was purified twice by silica gel chromatography (0-30% EtOAc/CH2Cl2, then 10-80% EtOAc/hexanes+2% AcOH) to give 23 mg of the title compound as a white solid. MS: (+) m/z 448.35 (M+1).

Workup

  1. temperaturewas cooled in an ice bath
  2. temperaturethe mixture was slowly warmed to r.t.
  3. stirringstirred for 16 h
  4. washwashed with 1 M HCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified twice by silica gel chromatography (0-30% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-c1b78676d5754a31915308d2def406ee
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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