Triethylamine → (+/-)-ethyl N-[4-(1-[{6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoyl]-beta-alaninate

HRID 1520964Notes

Reaction equation

HRID 1520964 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:10]1([C:13]2[CH:14]=[N:15][N:16]([C:18]3[N:23]=[CH:22][C:21]([NH:24][CH:25]([C:29]4[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=4)[CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=3)[CH:17]=2)[CH2:12][CH2:11]1.O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl.O>[CH:10]1([C:13]2[CH:14]=[N:15][N:16]([C:18]3[N:23]=[CH:22][C:21]([NH:24][CH:25]([C:29]4[CH:37]=[CH:36][C:32]([C:33]([NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:34])=[CH:31][CH:30]=4)[CH2:26][CH2:27][CH3:28])=[CH:20][CH:19]=3)[CH:17]=2)[CH2:12][CH2:11]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68157702(+/-)-4-(1-{[6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 86669098(+/-)-ethyl N-[4-(1-[{6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoyl]-beta-alaninate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of ethyl 3-aminopropionate hydrochloride (31 mg, 0.27 mmol), (+/−)-4-(1-{[6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]amino}butyl)benzoic acid (0.050 g, 0.13 mmol), hydroxybenzotriazole hydrate (0.020 g, 0.13 mmol), and triethylamine (76 ul, 0.55 mmol) in dichloromethane (1.3 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38.9 g, 201 mmol) (28 mg, 0.15 mmol) at rt. The mixture was stirred for 2 hours at ambient temperature. The reaction was diluted with water and the organic layer was separated. The aqueous layer was extracted with dichloromethane (2×) and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was used without further purification.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-0629272b78e040798639aed0bc85f1cc
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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