Triethylamine → HCID 67236480, compound

HRID 2092174Notes

Reaction equation

HRID 2092174 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 30 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-efa391d3648448d9970e5af72efd6ee5
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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