Dimethylformamide → HCID 11338034, compound

HRID 734742Notes

Reaction equation

HRID 734742 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([OH:19])=O.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH:31]1[C:39]2[C:34](=[CH:35][C:36]([NH2:40])=[CH:37][CH:38]=2)[CH:33]=[N:32]1>C(Cl)Cl.N1C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([NH:40][C:36]1[CH:35]=[C:34]2[C:39](=[CH:38][CH:37]=1)[NH:31][N:32]=[CH:33]2)=[O:19]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 880121H-Indazol-5-amineHCID 68830561HCID 68830561, compound

Product 1

HCID 11338034HCID 11338034, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 70, Step 2 (80 mg, 0.30 mmol) was dissolved in CH2Cl2 (4 mL) under Argon. DMF (20 μL) was added, followed by oxalyl chloride (27 μL, 0.30 mmol). This mixture was stirred at rt for 30 min, then the resultant yellow solution was added to a solution of 1H-indazol-5-amine (44 mg, 0.33 mmol) in pyridine (3 mL) at −15° C. under Ar. After stirring at −15° C. for 15 min, the reaction mixture was allowed to warm to rt over 1 h. The mixture was poured into EtOAc (50 mL), washed sequentially with aq. NH4Cl (20 mL), NaOH (10 mL, 2.5 N), HCl (10 mL, 1.0 N) and then brine. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was triturated with 10% ethyl acetate/10% ether/80% hexanes to afford the title compound (56 mg, 49%). MS (ES+) m/e 383 [M+H]+.

Workup

  1. stirringAfter stirring at −15° C. for 15 min
  2. temperatureto warm to rt over 1 h
  3. washwashed sequentially with aq. NH4Cl (20 mL), NaOH (10 mL, 2.5 N), HCl (10 mL, 1.0 N)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with 10% ethyl acetate/10% ether/80% hexanes

Sources & evidence

ORD record
ord-85152ea6b8c94fb4977d89e6ffbfbb2b
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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