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Thioglycolic Acid → (R)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80810
Notes
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Reaction equation

HRID 80810 reaction equation
[CH:1]([C:4]1[CH:8]=[C:7]([N:9]2[CH2:57][CH2:56][C:12]3[N:13]=[C:14]([C:36]4[CH:44]=[CH:43][CH:42]=[C:41]5[C:37]=4[C:38]([CH3:55])=[CH:39][N:40]5[S:45]([C:48]4[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=4)(=[O:47])=[O:46])[N:15]=[C:16]([N:17]4[CH2:22][CH2:21][N:20](S(C5C=CC=CC=5[N+]([O-])=O)(=O)=O)[C@H:19]([CH3:35])[CH2:18]4)[C:11]=3[CH2:10]2)[N:6]([CH3:58])[N:5]=1)([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1.SCC(O)=O>CN(C=O)C.O.ClCCl>[CH:1]([C:4]1[CH:8]=[C:7]([N:9]2[CH2:57][CH2:56][C:12]3[N:13]=[C:14]([C:36]4[CH:44]=[CH:43][CH:42]=[C:41]5[C:37]=4[C:38]([CH3:55])=[CH:39][N:40]5[S:45]([C:48]4[CH:49]=[CH:50][C:51]([CH3:52])=[CH:53][CH:54]=4)(=[O:46])=[O:47])[N:15]=[C:16]([N:17]4[CH2:22][CH2:21][NH:20][C@H:19]([CH3:35])[CH2:18]4)[C:11]=3[CH2:10]2)[N:6]([CH3:58])[N:5]=1)([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 1133Thioglycolic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 71240484HCID 71240484, compound

Product 1

HCID 71240581(R)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-((2-nitrophenyl)sulfonyl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (105 mg, 0.127 mmol) in DMF (3 mL) was added DBU (0.1 mL, 0.64 mmol) followed by 2-mercaptoacetic acid (0.018 mL, 0.255 mmol). The mixture was stirred for 3 hours and then diluted with water and dichloromethane. The layers were separated and the aqueous layer was extracted three additional times with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The resulting residue was purified via silica gel flash chromatography [4-25% (2 M NH3 in MeOH)/DCM] to provide (R)-6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 639.4 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted three additional times with dichloromethane
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified via silica gel flash chromatography [4-25% (2 M NH3 in MeOH)/DCM]

Sources & evidence

ORD record
ord-df0755466f0540289aa0b3a87923e88c
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846656B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes