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1,5-Dibromopentane → cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanone

HRID 133544
Notes
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Reaction equation

HRID 133544 reaction equation
[NH2:1][C:2]1[C:10]2[C:9]3[CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:5]=[C:4]([CH3:14])[C:3]=1[C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>CN(C=O)C>[CH:17]1([C:15]([C:3]2[C:4]([CH3:14])=[N:5][C:6]3[S:7][C:8]4[CH2:13][CH2:12][CH2:11][C:9]=4[C:10]=3[C:2]=2[N:1]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:16])[CH2:19][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 68896523(4-amino-6-methyl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-cyclopropyl-methanone

Product 1

HCID 11688694cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanoneYield 54%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a stirred solution of 12 mg (0.044 mmol) of (4-amino-6-methyl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-cyclopropyl-methanone in 2 ml DMF was added 3.0 mg (0.066 mmol) NaH (55% in oil). After 20 minutes, 10 □l (0.044 mmol) of 1,5-dibromo-pentane and stirring was continued at RT over the night. The mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 8 mg (54%) cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanone as a white solid. ES-MS m/e (%): 341 (M+H+, 100).

Workup

  1. customwas continued at RT over the night
  2. additionThe mixture was poured onto water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34056c9d4db34264a74cc4456791b51e
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07390903B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes