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Triethylamine → 2-Methylpentane

HRID 1183027
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Reaction equation

HRID 1183027 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:17][CH2:18][CH3:19])[CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].C(N(CC)CC)C.[C:27]([O:31][C:32](=[O:59])[N:33](/[C:45](=[N:51]/[C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])/N1C=CC=N1)[CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)([CH3:30])([CH3:29])[CH3:28].CCOC(C)=O>CN(C=O)C.O>[CH3:34][CH2:35][CH2:36][CH:37]([CH3:42])[CH3:38].[NH2:14][C:13]1[C:8]([C:6](=[O:7])[NH:5][CH2:4][C@H:3]([CH2:17][CH2:18][CH3:19])[NH:2]/[C:45](=[N:51]\[C:52](=[O:53])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])/[N:33]([CH2:34][CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[C:32](=[O:59])[O:31][C:27]([CH3:28])([CH3:30])[CH3:29])=[N:9][C:10]([Cl:16])=[C:11]([NH2:15])[N:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochlorideHCID 87204231tert-butyl N-[3-(4-methoxyphenyl)propyl]-N-[(Z)-N-[(2-methylpropan-2-yl)oxycarbonyl]-C-pyrazol-1-ylcarbonimidoyl]carbamate2×

Product 2

HCID 78922-Methylpentane
HCID 178448282
HCID 178448282, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride (Example 4) (0.2 g, 0.73 mmol) in DMF (3 mL) is added triethylamine (0.22 mL, 1.54 mmol) followed by {[(Z)-tert-Butoxycarbonylimino]-pyrazol-1-yl-methyl}-[3-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester (Intermediate E) and the resulting deep yellow solution is stirred at RT for 3 days. The reaction mixture is diluted with water (50 mL) and extracted with EtOAc (100 mL). The organic phase is washed with water (50 ml), dried (MgSO4), and the solvent removed in vacuo to afford a yellow oil. Chromatography (SiO2, EtOAc:iso-hexane, gradient 0-100%) affords (S,E)-tert-butyl 1-(3,5-diamino-6-chloropyrazin-2-yl)-7-(3-(4-methoxyphenyl)propyl)-10,10-dimethyl-1,8-dioxo-4-propyl-9-oxa-2,5,7-triazaundecan-6-ylidenecarbamate as a colourless oil. [M+H]+ 663.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. washThe organic phase is washed with water (50 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford a yellow oil

Sources & evidence

ORD record
ord-145f8ae9c7254d80ae745ec4628b8ab5
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08664228B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes