Triethylamine → HCID 11258649, compound

HRID 1833264Notes

Reaction equation

HRID 1833264 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].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.C(O)(=O)/C=C/C(O)=O.[NH2:51][CH2:52][CH2:53][C:54]#[N:55].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:52]([CH2:53][CH2:54][NH:55][C:25]([C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]([C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[N:8][CH:7]=1)=[O:26])#[N:51]

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 6433176Propanenitrile, 3-amino-, (2E)-2-butenedioate (1:1)HCID 11394498HCID 11394498, compound

Product 1

HCID 11258649HCID 11258649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6,7-dimethoxy-1-(3-methoxy-benzoyl)-isoquinoline-4-carboxylic acid (170 mg, 0.46 mmol) in dry, N,N-dimethylformamide (5 mL) was chilled in an ice bath under argon. With stirring, triethylamine (97 uL, 0.69 mmol) and isobutylchloroformate (72 uL, 0.56 uL) were added. The solution was stirred for 30 min and then 3-aminopropionitrile fumarate (118 mg, 0.92 mmol) and triethylamine (250 uL, 1.79 mmol) were added. The solution was allowed to warmed to room temperature with stirring overnight. The reaction mixture was poured into a 2% aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3×25 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 107 mg (55%) of an off white solid and used without further purification: APCI-MS m/e calcd for C23H21N3O5(M−H+) 420.4, found 420.0; 1H NMR (300 MHz) compatible.

Workup

  1. stirringThe solution was stirred for 30 min
  2. stirringwith stirring overnight
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford 107 mg (55%) of an off white solid
  8. customused without further purification

Sources & evidence

ORD record
ord-8dd6b8bc79f8489ea7b95f33350e8edf
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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