3-Amino-5-methylisoxazole → HCID 67235997, compound

HRID 1748344Notes

Reaction equation

HRID 1748344 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:18][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:19])[NH:4][CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:33][C:34]1[O:38][N:37]=[C:36]([NH2:39])[CH:35]=1.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>C1COCC1>[CH3:20][C:2]1([CH3:1])[CH2:18][N:7]2[C:8]3[CH:9]=[C:10]([C:15]([NH:39][C:36]4[CH:35]=[C:34]([CH3:33])[O:38][N:37]=4)=[O:17])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:19])[NH:4][CH2:3]1

Participants

6

Reactant 4

HCID 661723-Amino-5-methylisoxazoleHCID 682631,1'-CarbonyldiimidazoleHCID 67235538HCID 67235538, compoundHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 67235997HCID 67235997, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4,4-dimethyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (100 mg, 0.37 mmol) in THF (2 mL) is added 1,1′-carbonyldiimidazole (149 mg, 0.92 mmol). The reaction mixture is heated at 55° C. for 1 h. The mixture is cooled to room temperature and 5-methyl-3-aminoisoxazole (144 mg, 1.47 mmol) is added. After stifling 10 min, 1,8-diazabicycloundec-7-ene (0.14 mL, 0.92 mmol) is added and the reaction is heated at 60° C. for 16 h. After cooling to room temperature, the solvent is evaporated and the residue is purified by preparative HPLC using 10-85% acetonitrile/water with 0.1% TFA to afford the title compound (79 mg, 61%). LCMS (ESMS): m/z 353.45 (M+H+).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. temperaturethe reaction is heated at 60° C. for 16 h
  3. temperatureAfter cooling to room temperature
  4. customthe solvent is evaporated
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-8bb8e2564b784c779d19afe11309edb9
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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