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Dimethylformamide → HCID 67131174, compound

HRID 1678639
Notes
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Reaction equation

HRID 1678639 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([CH:19]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[OH:20])=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[N:11]2)=[CH:6][CH:5]=1.COC(=O)[C:30]1[CH:35]=[CH:34][C:33](CCl)=[CH:32][CH:31]=1.C1C[O:42][CH2:41]C1.[CH3:44]S(C)=O.CN([CH:51]=[O:52])C>>[CH3:41][O:42][C:51](=[O:52])[C:24]1[CH:23]=[CH:22][C:21]([C:19]([C:18]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=3)[N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[CH:13]3)([CH:32]2[CH2:31][CH2:30][CH2:35][CH2:34][CH2:33]2)[O:20][CH3:44])=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 36664Methyl 4-(chloromethyl)benzoateHCID 21830753dimethylsulfoxide THFHCID 67130979[2-(4-Chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-methanol

Product 1

HCID 67131174HCID 67131174, compound
Yield 22%

Procedure

Sodium hydride (14 mg, 293 umol) was added to an ice cold solution of [2-(4-chloro-phenyl)-2H-indazol-3-yl]-cyclohexyl-methanol (50 mg, 147 umol; example 10.1) in DMF (4.5 ml) under an argon atmosphere. After 30 min. methyl-4-(chloromethyl)benzoate (41 mg, 220 umol; CAS Reg. No. 34040-64-7) was added. The mixture was stirred at ambient temperature for 5 h, poured onto ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the crude product as brown oil which was purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water to give the title compound (16 mg, 33 μmol; 22%) as yellow solid. MS: m/e=489.4 [M+H+].

Workup

  1. addition34040-64-7) was added
  2. extractionextracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customto give the crude product as brown oil which
  8. customwas purified by preparative HPLC on reversed phase
  9. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-8366ed01ed194d7aab678679114a9b28
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008505B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes