Dimethylformamide → HCID 57845284, compound

HRID 734741Notes

Reaction equation

HRID 734741 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.[F:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[N:37][NH:38]2)=[CH:34][C:33]=1[NH2:41]>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:41][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][C:32]=1[F:31])[NH:38][N:37]=[CH:36]2)=[O:19]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 450905046-fluoro-1H-indazol-5-amineHCID 68830561HCID 68830561, compound

Product 1

HCID 57845284HCID 57845284, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 2 (40 mg, 0.15 mmol) was suspended in CH2Cl2 (2 mL) under Ar. DMF (10 μL) was added, followed by oxalyl chloride (13 μL, 0.15 mmol). This mixture was stirred at rt for 30 min, then the resultant yellow solution was added to a −15° C. solution of 6-fluoro-1H-indazol-5-amine (25 mg, 0.17 mmol) in pyridine (2 mL). 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 satd. NaCl. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was triturated with 10% EtOAc/10% ether/80% hexanes to afford the title compound (34 mg, 57%). MS (ES+) m/e 401 [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% EtOAc/10% ether/80% hexanes

Sources & evidence

ORD record
ord-0543b3fd3f984d978042a4685eb89950
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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