Diethylamine → 1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid diethylamide

HRID 2101147Notes

Reaction equation

HRID 2101147 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH:6]([O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=O)=[CH:17][CH:18]=2)[CH:13]=[C:12]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[N:11]=1)([CH3:8])[CH3:7].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([N:3]([CH2:4][CH3:5])[C:20]([C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[C:10]([O:9][CH:6]([CH3:7])[CH3:8])=[N:11][C:12]([NH:23][C:24]1[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=1)=[CH:13]2)=[O:22])[CH3:2]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 577994701-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid

Product 1

HCID 577997941-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid diethylamideYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Diethylamine (14 ul) and triethylamine (17 ul) in CH2Cl2 (5 ml) was added to 1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-6-carboxylic acid (33 mg), HOBt (18 mg), EDCI (25 mg) at 0° C. in order. The mixture was stirred at room temperature for 3 hrs and washed with 8% NaOH, water and brine, dried with anhydrous sodium sulfate and concentrated. The residue was purified by preparative LC-MS to give 31 mg of product as yellow solid. (80% yield). LC-MS: m/e 382 (MH+).

Workup

  1. washwashed with 8% NaOH, water and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-112937a878954c769134b708f4b58230
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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