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Diisopropylethylamine → (6-Chloropyrimidin-4-yl)-(octahydroindol-1-yl)-methanone

HRID 74510
Notes
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Reaction equation

HRID 74510 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.CCN(C(C)C)C(C)C.[NH:20]1[CH:28]2[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:22][CH2:21]1>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:20]2[CH:28]3[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:22][CH2:21]2)=[O:9])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 107275Octahydro-1H-indoleHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58386728(6-Chloropyrimidin-4-yl)-(octahydroindol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.517 g (2.92 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 10 mL dichloromethane were combined with 1.07 mL (6.00 mmol) DIPEA. 0.73 g (2.92 mmol) octahydroindole in 10 mL DCM was slowly added dropwise. After 2 h stirring at RT the mixture was diluted with dichloromethane and extracted with water. The organic phase was separated off, dried on sodium sulphate, filtered, evaporated down i. vac. and dried.

Workup

  1. extractionextracted with water
  2. customThe organic phase was separated off
  3. customdried on sodium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customand dried

Sources & evidence

ORD record
ord-d9e6d1a79cb5434b9b413788f1e27a35
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes