1H-Indazol-5-amine → HCID 10203025, compound

HRID 1991446Notes

Reaction equation

HRID 1991446 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.CC(C)([O-])C.[K+].C(S[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[C:22]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[C:32]([F:42])[CH:31]=2)[N:21]=1)C.CO.ClCCl>CN(C)C=O>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[C:22]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)=[C:32]([F:42])[CH:31]=4)[N:21]=3)=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

6

Reactant 4

HCID 880121H-Indazol-5-amineHCID 21226129Dichloromethane methanolHCID 23665647Potassium tert-butoxideHCID 68520786HCID 68520786, compound

Product 1

HCID 10203025HCID 10203025, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5-aminoindazole (0.020 g, 0.15 mmol) in dry N,N-dimethylformamide (4 mL) was added dropwise to a solution of potassium t-butoxide (0.017 g, 0.15 mmol) in dry N,N-dimethylformamide (1 mL). The reaction mixture went from green to red within a 20-minute period, and the contents were stirred at room temperature for 1 hour before the flask was treated with a solution of the compound of Example 37 (0.050 g, 0.14 mmol) in dry N,N-dimethylformamide (2 mL). The contents were stirred at room temperature for 2 hours, at which time TLC (silica gel 60, 5% methanol/dichloromethane, UV detection) analysis indicated complete consumption of starting quinazoline. The reaction mixture was poured into ethyl acetate (20 mL), and the organics were washed with brine (20 mL, 3×30 mL), dried over sodium sulfate and concentrated. The material was air-dried for 2 hours to give the product (0.031 g, 51%) as a pale-green solid. The NMR data was identical to that obtained in Example 5.

Workup

  1. customred within a 20-minute
  2. customconsumption of starting quinazoline
  3. additionThe reaction mixture was poured into ethyl acetate (20 mL)
  4. washthe organics were washed with brine (20 mL, 3×30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe material was air-dried for 2 hours

Sources & evidence

ORD record
ord-05524118fec34185a8c9327751d2fc48
Source dataset
uspto-grants-2010_01
Patent number
US07645878B2

Reaction notes

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