Trifluoroacetic acid → 6-bromo-4-(((3aS,4R,5R,6aS)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide TFA salt

HRID 877734Notes

Reaction equation

HRID 877734 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]2[C:16]([NH:17][C@@H:18]3[CH2:32][C@@H:21]4[CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][C@@H:20]4[C@H:19]3[CH3:33])=[C:15]([C:34](=[O:36])[NH2:35])[CH:14]=[N:13][N:12]2[CH:37]=1>ClCCl>[OH:5][C:3]([C:2]([F:7])([F:6])[F:1])=[O:4].[Br:8][C:9]1[CH:10]=[C:11]2[C:16]([NH:17][C@@H:18]3[CH2:32][C@@H:21]4[CH2:22][NH:23][CH2:24][C@@H:20]4[C@H:19]3[CH3:33])=[C:15]([C:34]([NH2:35])=[O:36])[CH:14]=[N:13][N:12]2[CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68291216(3aS,4R,5R,6aS)-tert-butyl 5-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 867078986-bromo-4-(((3aS,4R,5R,6aS)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide TFA saltYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL, 12.98 mmol) was added to a solution of (3 aS,4R,5R,6aS)-tert-butyl 5-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (250 mg, 0.523 mmol) in dichloromethane (2 mL). After stirring for 1 h at room temperature, the mixture was concentrated and dried under high vacuum to give 6-bromo-4-(((3aS,4R,5R,6aS)-4-methyloctahydrocyclopenta[c]pyrrol-5-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide TFA salt (255 mg). 1H NMR (400 MHz, methanol-d4) δ ppm 8.15 (1 H, s), 7.66 (1 H, d, J=1.54 Hz), 7.06 (1 H, d, J=1.54 Hz), 4.03-4.34 (1 H, m), 3.31-3.59 (3 H, m), 3.01-3.25 (2 H, m), 2.53-2.83 (2 H, m), 1.60-1.84 (1 H, m), 1.36-1.60 (1 H, m), 1.17 (3 H, d); MS (ES+) m/z: 378.1, 380.1 (M+H).

Workup

  1. concentrationthe mixture was concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-20fbc95d584041f0a4f4cb6226d5c687
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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