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Water → Tert-butyl 4-(2-(3-chloropyrazin-2-YL)-2-methylpropanamido)piperidine-1-carboxylate

HRID 707278
Notes
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Reaction equation

HRID 707278 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([NH:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acid

Product 1

HCID 86694146Tert-butyl 4-(2-(3-chloropyrazin-2-YL)-2-methylpropanamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (2.0 g, 9.97 mmol), tert-butyl 4-amino-1-piperidinecarboxylate (2.396 g, 11.96 mmol), DIEA (2.61 ml, 14.95 mmol), and hatu (4.17 g, 10.97 mmol) in DMF (30 mL) was stirred at RT overnight. The reaction mixture was then heated to 55° C. for 4 h, cooled, and H2O was added, the light brown solid was collected, dried and used in the next step (3.1 g, 81%). MS (M+1): 383.1

Workup

  1. temperatureThe reaction mixture was then heated to 55° C. for 4 h
  2. temperaturecooled
  3. customthe light brown solid was collected
  4. customdried

Sources & evidence

ORD record
ord-32bab38d8b9442eeb70b01495f62e8f5
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes