Hydrochloric Acid → Formic acid N-(6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-6-{[3-methyl-4-(1-methylethyl)-1-piperazinyl]methyl}-2-pyridinecarboxamide

HRID 1695780Notes

Reaction equation

HRID 1695780 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][C:12]2[CH:20]=[C:19]([C:21]3[CH:22]=[N:23][C:24]([Cl:32])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=3)[CH:18]=[C:17]3[C:13]=2[CH:14]=[N:15][N:16]3S(C2C=CC=CC=2)(=O)=O)=[O:10])[CH:6]=[CH:5][CH:4]=1.[CH3:42][CH:43]1[CH2:48][NH:47][CH2:46][CH2:45][N:44]1[CH:49]([CH3:51])[CH3:50].[OH-:52].[Na+].Cl>CC(O)C.CS(C)=O>[CH:9]([OH:10])=[O:52].[Cl:32][C:24]1[N:23]=[CH:22][C:21]([C:19]2[CH:18]=[C:17]3[C:13]([CH:14]=[N:15][NH:16]3)=[C:12]([NH:11][C:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:47]4[CH2:46][CH2:45][N:44]([CH:49]([CH3:51])[CH3:50])[CH:43]([CH3:42])[CH2:48]4)[N:8]=3)=[O:10])[CH:20]=2)=[CH:26][C:25]=1[NH:27][S:28]([CH3:31])(=[O:29])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 177503702-Methyl-1-(propan-2-yl)piperazineHCID 582558416-(Chloromethyl)-N-[6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide

Product 1

HCID 86653312Formic acid N-(6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-6-{[3-methyl-4-(1-methylethyl)-1-piperazinyl]methyl}-2-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

6-(Chloromethyl)-N-[6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide (50 mg, 0.079 mmol) and 2-methyl-1-(1-methylethyl)piperazine (0.5 ml, 0.047 mmol) were placed in a vial and heated in a microwave at 90° C. for 15 min. The amine was blown off under a stream of nitrogen to give an orange gum which was suspended in IPA (2 ml) and 2M NaOH (1 ml) was added. The mixture was stirred at room temperature for 2 hours then neutralised with 2M HCl (aq.) and the solvent was blown off under a stream of nitrogen. The residue was dissolved in DMSO (2 ml) (insoluble salt was filtered off through a filter tube) and purified by MDAP (Method E). The product-containing fractions were concentrated under a stream of nitrogen to give a white solid which was freeze dried to afford the title compound as a white solid (14 mg).

Workup

  1. customto give an orange gum which
  2. custompurified by MDAP (Method E)
  3. concentrationThe product-containing fractions were concentrated under a stream of nitrogen
  4. customto give a white solid which
  5. customdried

Sources & evidence

ORD record
ord-fe393373b1e74922baa38d1ac3fdca49
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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