Isoquinoline-1-carboxylic acid → HCID 69601193, compound

HRID 891189Notes

Reaction equation

HRID 891189 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][N:5]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([NH2:12])[C:6]1=[O:13].[C:15]1([C:25]([OH:27])=O)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1.ON1C2C=CC=C[C:32]=2N=N1>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:2][C:3](=[O:14])[CH2:4][N:5]1[CH2:11][CH:10]=[CH:9][CH2:8][CH:7]([NH:12][C:25]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[O:27])[C:6]1=[O:13])[CH3:32]

Participants

6

Reactant 3

HCID 68092Isoquinoline-1-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 23598686HCID 23598686, compound

Product 1

HCID 69601193HCID 69601193, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

(3-amino-2-oxo-2,3,4,7-tetrahydroazepin-1-yl) acetic acid methyl ester, 3, (0.365 g, 1.68 mmol) is dissolved in 1:1 CH2Cl2/DMF and 1-isoquinoline-carboxylic acid (1.4 g, 8.1 mmol), 1-hydroxybenzotriazole (0.35 g, 2.6 mmol), and 1-(3-dimethyl-aminopropyl)-3-ethyl-carbodiimide hydrochloride (0.5 g, 2.6 mmol) are added. The resulting solution is stirred at room temperature for 12 hours, diluted with EtOAc, washed with saturated NaHCO3 then brine, and dried (MgSO4). The solvent is removed in vacuo and the resulting residue is purified over silica gel (EtOAc/hexane) to afford the desired product.

Workup

  1. additionare added
  2. washwashed with saturated NaHCO3
  3. dry with materialbrine, and dried (MgSO4)
  4. customThe solvent is removed in vacuo
  5. customthe resulting residue is purified over silica gel (EtOAc/hexane)

Sources & evidence

ORD record
ord-46fc8dc708ae4769b2a931131d35c1ef
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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