Water → HCID 178522746, compound

HRID 2039787Notes

Reaction equation

HRID 2039787 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH4+].[Cl-].[C:7]12([CH2:17][NH:18][C:19]([C:21]3[C:22]4[N:23]([N:27]=[C:28]([CH2:30][CH2:31][C:32]#[N:33])[CH:29]=4)[CH:24]=[CH:25][CH:26]=3)=[O:20])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.O>CS(C)=O>[C:7]12([CH2:17][NH:18][C:19]([C:21]3[C:22]4[N:23]([N:27]=[C:28]([CH2:30][CH2:31][C:32]5[NH:33][N:3]=[N:2][N:1]=5)[CH:29]=4)[CH:24]=[CH:25][CH:26]=3)=[O:20])[CH2:14][CH:13]3[CH2:15][CH:9]([CH2:10][CH:11]([CH2:12]3)[CH2:16]1)[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 25095370HCID 25095370, compound

Product 1

HCID 178522746HCID 178522746, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

NaN3 (65 mg, 0.48 mmol) and NH4Cl (26 mg, 0.48 mmol) are added to a solution of 2-(2-cyano-ethyl)-pyrazolo[1,5-a]pyridine-4-carboxylic acid (adamantan-1-ylmethyl)-amide (58 mg, 0.16 mmol) in DMSO at rt. The mixture is heated to 130° C. for 6 h. Additional NaN3 (65 mg, 0.48 mmol) is added, and the mixture is heated for 14 h. The mixture is cooled to rt. H2O is added and pH is adjusted to about 7. The aqueous layer is extracted with EtOAc (3×15 mL), dried over Na2SO4 and the solvent is removed to dryness. The crude product is purified by PTLC (eluted with 2% MeOH in DCM) to give the title compound. 1H NMR (CDCl3): 8.49-8.47 (d, 1H), 7.52-7.50 (d, 1H), 6.79-6.69 (t, 1H), 6.69 (s, 1H), 6.40 (b, 1H), 3.44-3.41 (m, 2H), 3.31-3.29 (m, 2H), 3.20-3.19 (m, 2H), 2.00 (b, 3H), 1.74-1.60 (m, 12H). LC-MS m/z (M+H+): 406.07.

Workup

  1. temperaturethe mixture is heated for 14 h
  2. temperatureThe mixture is cooled to rt
  3. extractionThe aqueous layer is extracted with EtOAc (3×15 mL)
  4. dry with materialdried over Na2SO4
  5. customthe solvent is removed to dryness
  6. customThe crude product is purified by PTLC (eluted with 2% MeOH in DCM)

Sources & evidence

ORD record
ord-9c58343b4cec4276916db6e9efca3e91
Source dataset
uspto-grants-2013_11
Patent number
US08580812B2

Reaction notes

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