Sodium Bicarbonate → 7-[(2-Chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 887677Notes

Reaction equation

HRID 887677 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11]([O:15][C:16]([N:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[C:25]2[C:20](=[CH:21][C:22]([NH2:30])=[CH:23][CH:24]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:27][C:26]([CH3:29])([CH3:28])[C:25]2[C:20](=[CH:21][C:22]([NH:30][C:4]([C:3]3[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=3)=[O:5])=[CH:23][CH:24]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27745412-Chloronicotinoyl chlorideHCID 21959561Tert-butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 866032387-[(2-Chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloronicotinoyl chloride (3.52 g, 20 mmol, 1.0 eq.) and 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (5.52 g, 20 mmol, 1.0 eq.) in CH2Cl2 (100 mL) was added NaHCO3 (6.4 g, 80 mmol, 4.0 eq.). The mixture was stirred for 1 h at RT, then filtered and concentrated, followed by drying on a vacuum pump for 3 hours. 7-[(2-Chloro-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester was obtained as a white foamy solid. This title compound was used for next step without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customby drying on a vacuum pump for 3 hours

Sources & evidence

ORD record
ord-38d30b0d7a6a44588213771cb6a7e18f
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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