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Triethylamine → HCID 58465819, compound

HRID 1842452
Notes
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Reaction equation

HRID 1842452 reaction equation
[C:1]12([C:11](O)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:45]1[NH:50][CH2:49][CH2:48][N:47]2[CH:51]=[C:52]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:53]=[C:46]12.FC(F)(F)C(O)=O.C1NCCN2C=C(C(OCC)=O)C=C12>CN(C=O)C>[C:1]12([C:11]([N:50]3[CH2:49][CH2:48][N:47]4[CH:51]=[C:52]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:53]=[C:46]4[CH2:45]3)=[O:12])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 132351-Adamantanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58465607HCID 58465607, compoundHCID 67437166HCID 67437166, compound

Product 1

HCID 58465819
HCID 58465819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a microwave vial containing 1-adamantanecarboxylic acid (0.05 g, 0.283 mmol) was added HATU (0.11 g, 0.283 mmol), triethylamine (0.11 mL, 0.772 mmol) and DMF (1.5 mL). The solution was allowed to stir at rt for 30 minutes before ethyl 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate Intermediate 5 (0.05 g, 0.257 mmol) was added to the solution. The solution was then allowed to stir at rt overnight and then evaporated. To the resulting residue was added DCE (3 mL) and water (1 mL). After separation, the aqueous phase was extracted with DCE (2×3 mL). The combined organic phases were concentrated to give a crude ethyl 2-(1-adamantylcarbonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate as a solid.

Workup

  1. additionwas added to the solution
  2. customevaporated
  3. additionTo the resulting residue was added DCE (3 mL) and water (1 mL)
  4. customAfter separation
  5. extractionthe aqueous phase was extracted with DCE (2×3 mL)
  6. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-946fe944cfaf44a4810842c7a82e45c7
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes