Ethanolamine → HCID 72703161, compound

HRID 1777398Notes

Reaction equation

HRID 1777398 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH2:13][CH:14]=[O:15])[N:9]=2)=[N:6][CH:7]=1.[NH2:16][CH2:17][CH2:18]O.[N:20]1[N:21]([C:25]2[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)[N:22]=[CH:23][CH:24]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH2:13][CH:14]3[N:16]([C:27]([C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[N:21]4[N:20]=[CH:24][CH:23]=[N:22]4)=[O:29])[CH2:17][CH2:18][O:15]3)[N:9]=2)=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 213135922-(2H-1,2,3-Triazol-2-yl)benzoic acidHCID 86699775HCID 86699775, compound

Product 1

HCID 72703161HCID 72703161, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[1-(2,2-diethoxyethyl)-1H-pyrazol-3-yl]-5-fluoropyridine obtained in Reference Example 12 (4.0 g, 14.3 mmol) in CHCl3 (72 mL), TFA (6.4 mL, 85.9 mmol) was added, and the resulting mixture was stirred for 6 hours at 35° C. TFA (6.4 mL, 85.9 mmol) was further added thereto, and the mixture was stirred for 3 hours at 35° C. The reaction mixture was allowed to cool to room temperature, then an aqueous solution of NaHCO3 was added to the reaction mixture, followed by extraction with CHCl3. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over MgSO4, and then the drying agent was filtered off. The solvent was distilled off under reduced pressure to obtain [3-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]acetaldehyde (colorless oil). To a solution of [3-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]acetaldehyde in CHCl3 (36 mL), activated molecular sieve 4 A (29 g) and 2-aminoethanol (1.1 mL, 14.3 mmol) were added, and the resulting mixture was stirred for 48 hours at room temperature. The molecular sieve 4 A was filtered off through Celite®, and then the solvent was distilled off under reduced pressure to obtain a colorless oil. To a solution of the obtained colorless oil (0.10 g, 0.40 mmol) and 2-(2H-1,2,3-triazol-2-yl)benzoic acid (76 mg, 0.40 mmol) in DMF (0.4 mL), DIPEA (0.21 mL, 1.2 mmol) and HATU (0.16 g, 0.48 mmol) were added, and the resulting mixture was stirred for 48 hours at room temperature. The reaction mixture was purified by HPLC to obtain the title compound (40.8 mg) (colorless solid).

Workup

  1. filtrationThe molecular sieve 4 A was filtered off through Celite®
  2. distillationthe solvent was distilled off under reduced pressure
  3. customto obtain a colorless oil
  4. stirringthe resulting mixture was stirred for 48 hours at room temperature
  5. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-3d908c17b7b24b61b27da50bbd18d290
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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