Triethylamine → N-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethenesulfonamide

HRID 530967Notes

Reaction equation

HRID 530967 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:31]([CH:30]=[CH2:29])(=[O:33])=[O:32])=[CH:3][CH:4]=3)[C:16]=12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 516892Sodium BicarbonateHCID 58506796HCID 58506796, compound

Product 1

HCID 54756018N-(4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenyl)ethenesulfonamideYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dichloromethane (5 mL), compound 23 (45 mg, 0.168 mmol) and triethylamine (71 μL, 0.509 mmol) was cooled to 0° C. 2-chloro-1-ethane sulfonyl chloride (16 μL, 0.148 mmol) was added and the reaction was allowed to proceed for 1 hour prior to addition of saturated sodium bicarbonate (10 mL) and extraction with dichloromethane (2×10 mL). The combined organic layers were dried with MgSO4, filtered and concentrated in vacuo. The product was purified by preparative RP-HPLC and lyophilized (8.7 mg, 16% yield): 1H NMR (400 MHz, DMSO) δ 10.30 (s, 1H), 8.36 (s, 1H), 7.60 (d, J=8.5, 2H), 7.31 (d, J=8.6, 2H), 6.86 (dd, J=16.4, 9.9, 1H), 6.21 (d, J=16.4, 1H), 6.09 (d, J=9.9, 1H), 5.08 (hept, J=6.7, 2H), 1.49 (d, J=6.7, 6H); 13C NMR (100 MHz, DMSO) δ 155.44, 152.03, 151.64, 144.22, 138.54, 136.17, 129.25, 127.98, 127.41, 119.52, 96.95, 48.66, 21.75; [M+H]+ calculated for C16H18N6O2S 359.1, found 359.5.

Workup

  1. dry with materialThe combined organic layers were dried with MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe product was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-cbbe8363af9c4ba2b7f0f42cfd19f1f5
Source dataset
uspto-grants-2016_05
Patent number
US09353116B2

Reaction notes

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