Water → HCID 11360577, compound

HRID 1833274Notes

Reaction equation

HRID 1833274 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)=[N:8][CH:7]=[C:6]2[C:25](O)=[O:26].[Cl-].[NH4+].C([N:32](CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)=[N:8][CH:7]=[C:6]2[C:25]([NH2:32])=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 11394498HCID 11394498, compound

Product 1

HCID 11360577HCID 11360577, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6,7-dimethoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid (30mg, 81.7 mmol), ammonium chloride (43.5 mg. 0.817 mM) and triethylamine (0.115 mL, 0.817 mM) in 2 mL of dimethylformamide was stirred with O-benzotriazol-1-yl-N,N,N,N-tetramethyluronium hexafluorophosphate (61.9 mg. 0.163 mM) at room temperature for 20 hours. Poured into 20 mL of water and 20 mL of ethyl acetate, extracted ethyl acetate layer with saturated sodium bicarbonate, dried ethyl acetate solution. over anhydrous magnesium sulfate and evaporated to give 5.4 mg of an off-white solid pure product: APCI-MS m/e calcd for C20H18N2O6 (M+H.) 367.4, found 367; H NMR (300 MHz) compatible.

Workup

  1. extractionextracted ethyl acetate layer with saturated sodium bicarbonate, dried ethyl acetate solution
  2. customover anhydrous magnesium sulfate and evaporated

Sources & evidence

ORD record
ord-ae5c0f2fddc7429690556430f9b1672d
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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