3-Methoxybenzenesulfonyl chloride → 3-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide

HRID 1253490Notes

Reaction equation

HRID 1253490 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>N1C=CC=CC=1>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([S:35]([NH:26][C:22]2[CH:21]=[C:20]([C:19]#[C:18][C:17]3[CH:16]=[N:15][N:5]4[CH:6]=[C:7]([C:9]5[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=5)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=34)[CH:25]=[CH:24][N:23]=2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 27375043-Methoxybenzenesulfonyl chlorideHCID 584047124-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine

Product 1

HCID 673731343-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine (24 mg, 0.070 mmol) in pyridine (1400 μl), was added 3-methoxybenzenesulfonyl chloride (29 μl, 0.203 mmol). The reaction mixture was stirred for 72 hours at room temperature. The precipitated solid was filtered and the solid washed with 10 mL of dichloromethane. The solid was dried in vacuo to afford 3-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.75 (s, 1H); 8.34 (s, 1H); 8.26 (s, 1H); 8.06 (s, 1H); 7.99 (bs, 2H); 7.49-7.42 (m, 2H); 7.38 (s, 1H); 7.16-7.15 (m, 2H); 7.11 (s, 1H); 6.85 (bs, 1H); 4.07 (s, 3H); 3.87 (s, 3H); 3.79 (s, 3H). LRMS (ESI) calculated for C26H22N6O3S [M+H]+, 515.1; found 515.1.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washthe solid washed with 10 mL of dichloromethane
  3. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-c8e5144770bb45b3ae23332de933a2e1
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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