Sodium hydride → HCID 44476579, compound

HRID 2192529Notes

Reaction equation

HRID 2192529 reaction equation
[OH:1][NH:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1)=[NH:4].[Cl:15][C:16]1[CH:25]=[C:24]([O:26][CH:27]([CH3:29])[CH3:28])[CH:23]=[CH:22][C:17]=1[C:18](OC)=O.[H-].[Na+]>CN(C=O)C>[Cl:15][C:16]1[CH:25]=[C:24]([O:26][CH:27]([CH3:28])[CH3:29])[CH:23]=[CH:22][C:17]=1[C:18]1[O:1][N:2]=[C:3]([C:5]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:6]=2[CH:7]=[CH:8][N:9]=[CH:10]3)[N:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 58149895HCID 58149895, compoundHCID 178513273HCID 178513273, compound

Product 1

HCID 44476579HCID 44476579, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-hydroxy-5-isoquinolinecarboximidamide (D1, 30 mg, 0.160 mmol) was stirred in DMF (0.7 ml) with methyl 2-chloro-4-[(1-methylethyl)oxy]benzoate (D32; 40.3 mg, 0.176 mmol) and sodium hydride (60%; 4.61 mg, 0.115 mmol) in a Biotage Initiator microwave at 100° C. for 30 mins. The cooled mixture was concentrated under vacuum and the residue was purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)) to give the title compound as a pale yellow solid (8 mg).

Workup

  1. concentrationThe cooled mixture was concentrated under vacuum
  2. customthe residue was purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  3. washeluting with solvents A/B (A: Water+0.1% Formic acid, B

Sources & evidence

ORD record
ord-d3e76256d3b9459485571b58247b4727
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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