Triethylamine → HCID 71657549, compound

HRID 591359Notes

Reaction equation

HRID 591359 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]2[N:8]=[C:9](C(O)=O)[CH:10]=[C:3]12.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.CC[N:33]([CH2:36]C)CC.[F:38][C:39]1[CH:47]=[C:46]2[C:42]([CH2:43][CH2:44][N:45]2[CH:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)=[CH:41][CH:40]=1>C1COCC1>[F:38][C:39]1[CH:47]=[C:46]2[C:42]([CH2:43][CH2:44][N:45]2[CH:48]2[CH2:53][CH2:52][N:51]([C:36]([NH:33][C:9]3[CH:10]=[C:3]4[C:2](=[O:1])[NH:7][CH2:6][CH2:5][N:4]4[N:8]=3)=[O:21])[CH2:50][CH2:49]2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 220383846-Fluoro-1-(piperidin-4-yl)indolineHCID 552645784-Oxo-4,5,6,7-tetrahydropyrazolo[1,5-a] pyrazine-2-carboxylic acid

Product 1

HCID 71657549HCID 71657549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4,5,6,7-tetrahydro-4-oxo-pyrazolo[1,5-a]pyrazine-2-carboxylic acid (181 mg, 1.0 mmol) in THF (15 mL) was added diphenylphosphoryl azide (0.25 mL, 1.0 mmol) and Et3N (0.28 mL. 2.0 mmol). The resulting mixture was heated to reflux for 6 h and cooled to room temperature. Then 6-fluoro-1-(piperidin-4-yl)indoline (88 mg, 0.4 mmol) and Et3N (0.14 mL, 1.0 mmol) were added sequentially. The resulting mixture was stirred at room temperature for 24 h and concentrated. The resulting residue was purified by chromatography using EtOAc, then 2-5% MeOH/EtOAc as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)piperidine-1-carboxamide.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 6 h
  3. concentrationconcentrated
  4. customThe resulting residue was purified by chromatography

Sources & evidence

ORD record
ord-ca856f801a4e40709bd111546ae06473
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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