Potassium Carbonate → HCID 54517635, compound

HRID 1432971Notes

Reaction equation

HRID 1432971 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH:15]([CH3:19])[C:14]3=[O:20])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.Br[CH2:22][C:23]1[N:24]=[CH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[C:28]([Cl:33])[CH:27]=2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:22][C:23]4[N:24]=[CH:25][C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[C:28]([Cl:33])[CH:27]=5)[C@@H:15]([CH3:19])[C:14]3=[O:20])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17985192HCID 17985192, compoundHCID 53812518HCID 53812518, compound

Product 1

HCID 54517635HCID 54517635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-amino-quinazoline-7-ylmethyl)-3-methyl-piperazine-2-one, EXAMPLE 80, (0.06 g, 0.2 mmol) in 2 mL of DMF is added 3-bromomethyl-7-chloroisoquinoline, EXAMPLE 11, 0.052 g, 0.20 mmol), and K2CO3 (0.08 g, 0.06 mmol). After 16 h, the reaction mixture is concentrated to dryness The crude product is purified by RP-HPLC eluting with a gradient of 5% CH3CN/H2O (0.1% TFA) to 50% CH3CN/H2O (0.1% TFA). The product fractions are lyophilized to give the title compound as a tristrisfluoroacetic acid salt (0.06 g, 0.08 mmol) as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ9.79 (bs, 2H), 9.40 (s, 1H), 8.73 (s, 1H), 8.33 (d, 1H), 8.25 (s, 1H), 8.06 (s, 1H), 8.00 (d, 1H), 7.79 (d, 1H), 7.60 (m, 2H), 4.80 (AB, 2H), 4.72 (AB, 2H), 4.28 (m, 1H), 3.54 (m, 4H), 1.96 (d, 3H). MS (ion spray) 447, 449, (Cl pattern). Elemental analysis C28H25ClF6N6O6.3CF3CO2H.0.28H2O, cal C=45.38%, H=3.35%, N=10.58%; found C=45.38, H=3.35%, N=10.63%.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness The crude product
  2. customis purified by RP-HPLC
  3. washeluting with a gradient of 5% CH3CN/H2O (0.1% TFA) to 50% CH3CN/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-b1be642f9a28485dade7b71d529d0f7a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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