4-Methylmorpholine → HCID 59987525, compound

HRID 658503Notes

Reaction equation

HRID 658503 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([NH:14][C:15]3[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=3)[O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([OH:27])=O)[CH:20]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[NH2:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([NH:14][C:15]3[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=3)[O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[O:27])[CH:20]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 33944N-(2-Aminoethyl)piperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59252135HCID 59252135, compound

Product 1

HCID 59987525HCID 59987525, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[3-({[(1-methyl-1H-indazol-5-yl)amino]carbonyl}amino)phenoxy]-pyridine-2-carboxylic acid (0.07 g, 0.17 mmol) was dissolved in DMF (2.5 mL), followed by sequential addition of 1-(2-aminoethyl)piperidine (0.02 g, 0.17 mmol), 1-hydroxybenzotriazole (0.05 g, 0.38 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (0.05 g, 0.26 mmol), and N-methylmorpholine (0.04 g, 0.38 mmol). The mixture was stirred at room temperature for 12 h, and the solvent was removed in vacuo. The crude residue was dissolved in CH2Cl2 (10 mL), and washed with H2O (3 mL). The solvent was removed in vacuo, and the crude product was purified by preparative HPLC. The isolated product was washed with aq. Na2CO3 to give 0.07 g (78%) of the title compound. 1H-NMR (CD3OD) δ 8.51 (d, 1H), 7.91 (s, 1H), 7.84 (d, 1H), 7.59 (d, 1H), 7.50-7.46 (m, 2H), 7.41-7.36 (m, 2H), 7.26 (dd, 1H), 7.10 (dd, 1H), 6.81-6.77 (dd, 1H), 4.03 (s, 3H), 3.60 (t, 2H), 2.78-2.71 (m, 6H), 1.69-1.51 (m, 6H); MS LC-MS (M+H)+=514.3, RT=2.62 min.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe crude residue was dissolved in CH2Cl2 (10 mL)
  3. washwashed with H2O (3 mL)
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by preparative HPLC
  6. washThe isolated product was washed with aq. Na2CO3

Sources & evidence

ORD record
ord-3eaaa9fe067f46b6884ed2db92645e1c
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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