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Triethylamine → HCID 58394359, compound

HRID 2189206
Notes
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Reaction equation

HRID 2189206 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]([N:20]1[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[N:11]=[C:10]([NH:25][C@H:22]2[CH2:23][CH2:24][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:21]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2528862,4-DichloroquinazolineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 58394359HCID 58394359, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344Dichloromethane
Solvent

Procedure

A solution of 2,4-dichloroquinazoline (0.940 g, 4.70 mmol) in dichloromethane (50 mL) was treated with (S)-(−)-1-boc-3-aminopyrrolidine (0.863 mL, 4.70 mmol) followed by triethylamine (2 mL, 14.20 mmol) and the solution was stirred at room temperature for 36 hours. The mixture was diluted with water (20 mL) and extracted with diethyl ether (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a pale brown solid which was used without further purification.

Workup

  1. extractionextracted with diethyl ether (2×20 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d18e7fd9a9ee4f8886ea9d2219669e7f
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324226B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes