p-Toluenesulfonic acid monohydrate → 4-(((1R,3S)-3-amino-2,2,3-trimethylcyclopentyl)amino)-6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408989Notes

Reaction equation

HRID 1408989 reaction equation
C(OC([NH:8][C@@:9]1([CH3:37])[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:16]3[N:17]([CH:24]=[C:25]([C:27]([NH:29][NH:30][C:31]([S:33][CH3:34])=[S:32])=O)[CH:26]=3)[N:18]=[CH:19][C:20]=2[C:21](=[O:23])[NH2:22])[C:10]1([CH3:36])[CH3:35])=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:8][C@@:9]1([CH3:37])[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]2[C:16]3[N:17]([CH:24]=[C:25]([C:27]4[S:32][C:31]([S:33][CH3:34])=[N:30][N:29]=4)[CH:26]=3)[N:18]=[CH:19][C:20]=2[C:21]([NH2:22])=[O:23])[C:10]1([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86707721methyl 2-(4-(((1R,3S)-3-((tert-butoxycarbonyl)amino)-2,2,3-trimethylcyclopentyl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carbonyl)hydrazinecarbodithioate

Product 1

HCID 867077224-(((1R,3S)-3-amino-2,2,3-trimethylcyclopentyl)amino)-6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 208.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-(4-((1R,3S)-3-(tert-butoxycarbonylamino)-2,2,3-trimethylcyclopentylamino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carbonyl)hydrazinecarbodithioate (466.5 mg, 0.849 mmol) and p-toluenesulfonic acid monohydrate (404 mg, 2.122 mmol) in ethanol (4 mL) was heated to 120° C. for 50 minutes. The reaction mixture was concentrated to yield 4-(((1R,3S)-3-amino-2,2,3-trimethylcyclopentyl)amino)-6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (763 mg, 94% yield). MS (ES+) m/z: 432.08 (M+H); HPLC retention time: 2.493 min (analytical HPLC Method F).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-749990ba7f81444cb2db24fc6ed03979
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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