Triethylamine → HCID 178428725, compound

HRID 2059937Notes

Reaction equation

HRID 2059937 reaction equation
[OH:1][NH:2][C:3](=[NH:22])[C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8][CH2:7]2.C(N(CC)CC)C.[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42])[C:34](Cl)=[O:35]>ClCCl>[Cl:30][C:31]1[CH:32]=[C:33]([C:34]([O:1][NH:2][C:3](=[NH:22])[C:4]2[C:5]([CH3:21])=[C:6]3[C:11](=[CH:12][CH:13]=2)[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:8][CH2:7]3)=[O:35])[CH:37]=[CH:38][C:39]=1[O:40][CH:41]([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21710470HCID 21710470, compoundHCID 178428722HCID 178428722, compound

Product 1

HCID 178428725HCID 178428725, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 6-[(hydroxyamino)(imino)methyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 17; 435 mg; 1.42 mmol) in dichloromethane (10 ml) was added triethylamine (0.30 ml; 2.14 mmol) followed by 3-chloro-4-[(1-methylethyl)oxy]benzoyl chloride (Preparation 8; 365 mg; 1.57 mmol) in dichloromethane (5 ml). After 30 min, the reaction was concentrated, and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was further extracted with ethyl acetate, and the combined organic layers washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with a gradient of 10-50% ethyl acetate in cyclohexane gave the title compound as a white foam (413 mg).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. washthe combined organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with a gradient of 10-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-576851a69f5f452f98218ba6d6bbfd76
Source dataset
uspto-grants-2012_10
Patent number
US08278324B2

Reaction notes

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