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Pyridine → 6-(Chloromethyl)-N-[6-{6-(methyloxy)-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 1695729
Notes
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Reaction equation

HRID 1695729 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14]([O:17][CH3:18])=[N:15][CH:16]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25].N1C=CC=CC=1.[Cl:39][CH2:40][C:41]1[N:46]=[C:45]([C:47](Cl)=[O:48])[CH:44]=[CH:43][CH:42]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:39][CH2:40][C:41]1[N:46]=[C:45]([C:47]([NH:1][C:2]2[CH:10]=[C:9]([C:11]3[CH:16]=[N:15][C:14]([O:17][CH3:18])=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=3)[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][N:6]3[S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[O:48])[CH:44]=[CH:43][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 66911247N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamideHCID 866533026-(Chloromethyl)-2-pyridinecarbonyl chloride

Product 1

HCID 582558006-(Chloromethyl)-N-[6-{6-(methyloxy)-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide
Yield 25.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (750 mg, 1.584 mmol) was dissolved in DCM (20 ml), cooled to 0° C. before pyridine (0.192 mL, 2.376 mmol) was added. 6-(chloromethyl)-2-pyridinecarbonyl chloride (354 mg, 1.584 mmol) in DCM (10 ml) was then added dropwise over 15 mins and the reaction was stirred at 0° C. for 2 hr; ice was allowed to melt over this time. Saturated aqueous sodium bicarbonate solution (20 ml) was added to the mixture and it was stirred vigourously for 10 mins. The organic layer was separated using a hydrophobic frit, washed with water (20 ml) and concentrated in vacuo to give an orange oil. The oil was triturated with ether and the resulting solid was filtered off then pre-adsorbed onto silica. The silica was added to the top of a 50 g silica SPE cartridge that was subsequently eluted with 0-100% EtOAc/cyclohexane over 60 mins to afford the title compound as a pale yellow solid (253 mg).

Workup

  1. additionwas added
  2. stirringwas stirred vigourously for 10 mins
  3. customThe organic layer was separated
  4. washwashed with water (20 ml)
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil
  7. customThe oil was triturated with ether
  8. filtrationthe resulting solid was filtered off
  9. additionThe silica was added to the top of a 50 g silica SPE cartridge that
  10. washwas subsequently eluted with 0-100% EtOAc/cyclohexane over 60 mins

Sources & evidence

ORD record
ord-59b99b32c9e9474c9c760e1a6bfbf7f2
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163743B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes