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Water → 6-(Chloromethyl)-N-[6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide

HRID 520586
Notes
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Reaction equation

HRID 520586 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([NH2:28])[C:13]4[CH:14]=[N:15][N:16]([S:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.[Cl:38][CH2:39][C:40]1[N:45]=[C:44]([C:46](Cl)=[O:47])[CH:43]=[CH:42][CH:41]=1.O>C(Cl)(Cl)Cl>[Cl:38][CH2:39][C:40]1[N:45]=[C:44]([C:46]([NH:28][C:12]2[CH:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH:3]=[CH:2][NH:1]4)[CH:18]=[C:17]3[C:13]=2[CH:14]=[N:15][N:16]3[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[O:47])[CH:43]=[CH:42][CH:41]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 582680186-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amineHCID 866533026-(Chloromethyl)-2-pyridinecarbonyl chloride

Product 1

HCID 582679866-(Chloromethyl)-N-[6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-yl]-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To solution of 6-(1H-indol-4-yl)-1-(phenylsulfonyl)-1H-indazol-4-amine (1.37 g) in chloroform (30 ml) at 0° C. was added DIPEA (1.232 ml). 6-(Chloromethyl)-2-pyridinecarbonyl chloride (1.519 g, crude) in chloroform (15 ml) was added dropwise and the mixture was stirred at 0° C. for 15 min. Water (30 ml) was added and the mixture was extracted with DCM (50 ml), separating the layers by hydrophobic frit.

Workup

  1. extractionthe mixture was extracted with DCM (50 ml)
  2. customseparating the layers by hydrophobic frit

Sources & evidence

ORD record
ord-67681d003e40489a9c6417ba59fa386b
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09326987B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes