Triethylamine → HCID 69747061, compound

HRID 497460Notes

Reaction equation

HRID 497460 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 198005561,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylate

Product 1

HCID 69747061HCID 69747061, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a dry flask 5-amino-indazole-1-carboxylic acid t-butyl ester (1.4 g, 6.0 mmol) was dissolved in tetrahydrofuran (20 mL) and triethylamine (1.0 g, 9.9 mmol) were added and the reaction mixture cooled to 0° C. Phenyl chloroformate (1.0 g, 6.4 mmol) was added dropwise and the mixture was stirred an additional 15 minutes after the addition was complete. The reaction mixture was diluted with ethyl acetate, washed with water, and concentrated in vacuo. The crude material was purified by flash chromatography with 35% ethyl acetate in hexanes to give a white solid (1.9 g, 90%). 1H NMR (300 MHz, CDCl3), δ: 8.14 (d, J=10, 1H), 8.12 (s, 1H), 8.02 (bs, 1H), 7.40 (m, 3H), 7.24 (m, 4H), 1.73 (s, 9H).

Workup

  1. additionafter the addition
  2. washwashed with water
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography with 35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-82b05f4f9d02435a91b10f0b12fc6c37
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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