Hydrochloric Acid → N-((1S,3R,4S)-3-ethyl-4-(6-tosylpyrrolo[2,3-b][1,2, 3]triazolo[4,5-d]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide

HRID 1969681Notes

Reaction equation

HRID 1969681 reaction equation
[NH2:1][C:2]1[C:3]([NH:21][C@@H:22]2[C@H:26]([CH2:27][CH3:28])[CH2:25][C@H:24]([NH:29][S:30]([CH:33]3[CH2:35][CH2:34]3)(=[O:32])=[O:31])[CH2:23]2)=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.Cl.[N:37]([O-])=O.[Na+]>O>[CH2:27]([C@H:26]1[C@@H:22]([N:21]2[C:3]3=[C:4]4[CH:10]=[CH:9][N:8]([S:11]([C:14]5[CH:15]=[CH:16][C:17]([CH3:18])=[CH:19][CH:20]=5)(=[O:12])=[O:13])[C:5]4=[N:6][CH:7]=[C:2]3[N:1]=[N:37]2)[CH2:23][C@@H:24]([NH:29][S:30]([CH:33]2[CH2:35][CH2:34]2)(=[O:31])=[O:32])[CH2:25]1)[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 58557853N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide

Product 1

HCID 67998704N-((1S,3R,4S)-3-ethyl-4-(6-tosylpyrrolo[2,3-b][1,2, 3]triazolo[4,5-d]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-((1S,3S,4R)-3-(5-amino-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.15 g, 0.23 mmol, Example #23 Step I) and aqueous HCl (6 N, 1.0 mL, 6.00 mmol) was cooled to about 0° C. A solution of NaNO2 (0.022 g, 0.32 mmol) in water (0.2 mL) was added and the reaction was stirred at about 0° C. After about 3 h, the reaction was warmed to rt. After about 15.5 h, the reaction was filtered to collect the yellow solid by vacuum filtration, while washing with water (10 mL). The crude solid was purified by silica gel chromatograpy eluting with 0-20% EtOAc in DCM to give N-((1S,3R,4S)-3-ethyl-4-(6-tosylpyrrolo[2,3-b][1,2,3]triazolo[4,5-d]pyridin-1(6H)-yl)cyclopentyl)cyclopropanesulfonamide (0.088 g, 74%): LC/MS (Table 1, Method a) Rt=2.44 min; MS m/z: 529 (M+H)+.

Workup

  1. temperaturethe reaction was warmed to rt
  2. waitAfter about 15.5 h
  3. filtrationthe reaction was filtered
  4. customto collect the yellow solid
  5. filtrationby vacuum filtration
  6. washwhile washing with water (10 mL)
  7. customThe crude solid was purified by silica gel chromatograpy
  8. washeluting with 0-20% EtOAc in DCM

Sources & evidence

ORD record
ord-de11b8beae434133977af4e672d90bde
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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