Ethylmorpholine → HCID 89813140, compound

HRID 1481025Notes

Reaction equation

HRID 1481025 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21](O)=[O:22])[N:4]=1)#[N:2].C(N1CCOCC1)C.[NH2:32][C:33]([CH3:41])([CH3:40])[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21]([NH:32][C:33]([CH3:41])([CH3:40])[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[O:22])[N:4]=1)#[N:2]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 24973904HCID 24973904, compoundHCID 89812857HCID 89812857, compound

Product 1

HCID 89813140HCID 89813140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylic acid (47 mg, 0.15 mmol), N-ethylmorpholine (27 μL, 0.21 mmol), methyl 4-amino-4-methylpentanoate (crude as its acetic acid salt, 41 mg, 0.20 mmol), DCC (41 mg, 0.20 mmol) and HOBT (56 mg, 0.41 mmol) were suspended in CH2Cl2 (1 mL). The resulting mixture was stirred at room temperature for 20 hours. The reaction crude was filtered through a pad of celite and the filtrate was washed with sat'd NaHCO3 solution and H2O. The organic layer was dried over MgSO4, concentrated, and purified by flash chromatography (0-40% EtOAc/hexanes) to give the title compound in 12 mg. MS: (−) m/z 432.22 (M−1).

Workup

  1. customThe reaction crude
  2. filtrationwas filtered through a pad of celite
  3. washthe filtrate was washed with sat'd NaHCO3 solution and H2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c511bfa3c0d3431c9c9f22ad05032583
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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