Diisopropylethylamine → HCID 178419831, compound

HRID 2204647Notes

Reaction equation

HRID 2204647 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.Cl.[CH:14]1([NH:20][NH2:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>CC(O)(C)C>[CH:14]1([N:20]2[C:2]3=[C:3]4[CH:12]=[CH:11][NH:10][C:4]4=[N:5][CH:6]=[C:7]3[CH:8]=[N:21]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 207836Cyclohexylhydrazine hydrochlorideHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 178419831HCID 178419831, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution containing 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.100 g, 0.554 mmol, Adesis), cyclohexylhydrazine hydrochloride (0.125 g, 0.831 mmol) and DIEA (0.19 mL, 1.1 mmol) in t-BuOH (5 mL) was stirred at ambient temperature for about 1 h, then heated at about 70° C. for about 1 h, followed by heating in a Biotage microwave at about 200° C. for about 1 h. The insoluble residue was removed by filtration and the filtrate was subjected to purification by preparative RP-HPLC (Table 2, Method p) to yield 1-cyclohexyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.045 g, 0.187 mmol, 34%) as an off-white solid: LC/MS (Table 2, Method d,) Rt 2.13 min; m/z: 241 (M+H)+, 239 (M−H)−.

Workup

  1. temperatureheated at about 70° C. for about 1 h
  2. temperatureby heating in a Biotage microwave at about 200° C. for about 1 h
  3. customThe insoluble residue was removed by filtration
  4. customthe filtrate was subjected to purification by preparative RP-HPLC (Table 2, Method p)

Sources & evidence

ORD record
ord-bfe915de74924235add9fc8414441d7f
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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