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Triethylamine → ethyl 4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate

HRID 1408983
Notes
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Reaction equation

HRID 1408983 reaction equation
[NH2:1][C@@:2]1([CH3:27])[CH2:6][CH2:5][C@@H:4]([NH:7][C:8]2[C:9]3[N:10]([CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:19]=3)[N:11]=[CH:12][C:13]=2[C:14](=[O:16])[NH2:15])[C:3]1([CH3:26])[CH3:25].CCN(CC)CC.[O:35](C(OC(C)(C)C)=O)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=O>C1COCC1>[C:39]([O:38][C:36]([NH:1][C@@:2]1([CH3:27])[CH2:6][CH2:5][C@@H:4]([NH:7][C:8]2[C:9]3[N:10]([CH:17]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:19]=3)[N:11]=[CH:12][C:13]=2[C:14](=[O:16])[NH2:15])[C:3]1([CH3:26])[CH3:25])=[O:35])([CH3:42])([CH3:41])[CH3:40]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 68358616ethyl 4-((1R,3S)-3-amino-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate

Product 1

HCID 86707717ethyl 4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
70 °C

Procedure

A solution of ethyl 4-((1R,3S)-3-amino-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate (8.37 g, 22.42 mmol) and Et3N (6.25 mL, 44.8 mmol) in THF (100 mL) was added BOC2O (10.41 mL, 44.8 mmol), and then the reaction mixture was heated to 70° C. for 16 hrs. The reaction mixture was concentrated to afford ethyl 4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate. LC/MS (M+H)+=474.3.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1d24bdd3cc0b4e1a8ece7aa21d36be4f
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921368B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes