Triethylamine → HCID 67236480, compound

HRID 1158810Notes

Reaction equation

HRID 1158810 reaction equation
COC([N:5]1[C:13]2[C:8](=[C:9]([NH:14][C:15]([O:17]N3C(=O)CCC3=O)=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1)=O.[O:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[O:28][CH2:27][CH:26]1[CH2:35][NH2:36].C(N(C(C)C)CC)(C)C.C(N(CC)CC)C>CN(C)C=O.O.CO>[O:25]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[O:28][CH2:27][CH:26]1[CH2:35][NH:36][C:15]([NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[N:6][NH:5]2)=[O:17]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 150532-Aminomethyl-1,4-benzodioxaneHCID 81531DiisopropylethylamineHCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

Product 1

HCID 67236480HCID 67236480, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent3×HCID 6228DimethylformamideSolvent

Procedure

The product of Example 24D (635 mg, 1.9 mmol) was added to a solution of 1-(2,3-dihydro-1,4-benzodioxin-2-yl)methanamine (315 mg, 1.9 mmol) and diisopropylethylamine (0.34 mL, 1.9 mmol) in N,N-dimethylformamide (5 mL) under nitrogen atmosphere at ambient temperature. After 3 0 minutes the reaction solution was diluted with water (50 mL), the resulting precipitate was filtered off, washed with water and air-dried. The wet cake was added to a solution of methanol (25 mL), water (3 mL) and triethylamine (0.54 mL, 3.8 mmol). The mixture was refluxed for an hour, cooled to room temperature, diluted with water (100 mL), collected the white precipitate by filtration, rinsed with water and air-dried. The wet cake was vacuum dried to constant weight to provide the title compound (568 mg, 92%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ: 3.41-3.56 (m, 2H), 3.98 (dd, 1H), 4.26-4.33 (m, 1H), 4.36 (dd, 1H), 6.68 (t, 1H), 6.81-6.94 (m, 4H), 7.06 (d, 1H), 7.20 (t, 1H), 7.62 (d, 1H), 8.09 (s, 1H), 8.80 (s, 1H), 13.00 (s, 1H). MS (ESI) m/z: 325.1 (M+H)+; Anal. Calc'd for C17H16N4O3: C, 62.95; H, 4.97; N, 17.27. Found: C, 62.66; H, 4.83; N, 16.99.

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with water
  3. customair-dried
  4. temperatureThe mixture was refluxed for an hour
  5. customcollected the white precipitate
  6. filtrationby filtration
  7. washrinsed with water
  8. customair-dried
  9. customdried to constant weight

Sources & evidence

ORD record
ord-8e0b69c97f1d4c83885983e39cd882d1
Source dataset
uspto-grants-2010_10
Patent number
US07812019B2

Reaction notes

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