4-Methylmorpholine → HCID 10192997, compound

HRID 1823896Notes

Reaction equation

HRID 1823896 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.C1C=CC2N(O)N=NC=2C=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29](O)=[O:30])[CH:25]=[CH:26][CH:27]=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][C:29]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][N:6]=[CH:5]3)=[O:30])[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 158793-Chlorophenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 880121H-Indazol-5-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10192997HCID 10192997, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-aminoindazole (1 mmol), HOBt (1 mmol) and 3-chlorophenylacetic acid (1.1 mmol) in DMF (4 mL) was added N-methylmorpholine (1.1 mmol). After stirring for 10 minutes, EDC-HCl (1.1 mmol) was added and the reaction mixture stirred overnight at ambient temperature. The reaction mixture was concentrated and the residue purified by reverse phase preparative HPLC [Waters Delta-Pak C18, 15 uM, 100A column, gradient 10%–100% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 10 minutes at 25 mL/min] to afford compound I-6 (79 mg, 42%). 1H NMR (400 MHz, DMSO-d6) δ 3.68 (2H, s), 7.12–7.73 (6H, m), 8.00 (1H, s), 8.11 (1H, s), 10.10 (1H, s), 12.97 (1H, bs); MS (ES+): m/e=(M+H) 286.

Workup

  1. stirringthe reaction mixture stirred overnight at ambient temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by reverse phase preparative HPLC [Waters Delta-Pak C18, 15 uM, 100A column, gradient 10%–100% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 10 minutes at 25 mL/min]
  4. customto afford compound I-6 (79 mg, 42%)

Sources & evidence

ORD record
ord-6f8d8935d3684785acafe247d60f0532
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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