Perchloric Acid → HCID 178492923, compound

HRID 1754070Notes

Reaction equation

HRID 1754070 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]#[N:8].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[C:12]([O:18][CH3:19])[CH:11]=1.[N:20]#[C-:21].[CH2:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.Cl(O)(=O)(=O)=O>CO>[CH:22]1([NH:20][C:21]2[N:6]3[N:5]=[CH:4][C:3]([C:7]#[N:8])=[C:2]3[NH:1][C:14]=2[C:13]2[CH:16]=[CH:17][C:10]([F:9])=[CH:11][C:12]=2[O:18][CH3:19])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 855155-Amino-4-cyanopyrazoleHCID 27745374-Fluoro-2-methoxybenzaldehydeHCID 131733666HCID 131733666, compound

Product 1

HCID 178492923HCID 178492923, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear light yellow solution of 5-amino-1H-pyrazole-4-carbonitrile (169 mg, 1.56 mmol) and 4-fluoro-2-methoxybenzaldehyde (240 mg, 1.56 mmol) in methanol (3 mL) was added cyclopentane isonitrile (150 mg, 174 μL, 1.56 mmol) followed by perchloric acid (31.3 mg, 28.0 μL, 0.312 mmol) at RT under nitrogen atmosphere. The resulting light brown suspension was stirred for 15 h and during this period (within 1 minute) lot of solids were formed. The solids were collected by filtration and washed with methanol. After air drying, 175 mg (33% yield) of 3-(cyclopentylamino)-2-(4-fluoro-2-methoxyphenyl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile was isolated as an off-white solid. LC/MS calcd. for C18H18FN5O (m/e) 339.37, obsd. 340.0 (M+H, ES+).

Workup

  1. customwere formed
  2. filtrationThe solids were collected by filtration
  3. washwashed with methanol
  4. customAfter air drying

Sources & evidence

ORD record
ord-29e549c6f22f4261b3f4931a28d0df2c
Source dataset
uspto-grants-2015_10
Patent number
US09169215B2

Reaction notes

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