Water → HCID 68350400, compound

HRID 877820Notes

Reaction equation

HRID 877820 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](Cl)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1.[NH2:15][C@H:16]1[C@@H:20]([O:21][CH3:22])[CH2:19][N:18]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:17]1.C(N(CC)C(C)C)(C)C.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:15][C@H:16]3[C@@H:20]([O:21][CH3:22])[CH2:19][N:18]([C:23]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:24])[CH2:17]3)=[C:8]([C:11](=[O:12])[NH2:13])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide2×HCID 68350312HCID 68350312, compound2×

Product 1

HCID 68350400HCID 68350400, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 0.4 g, 1.46 mmol) in DMF (2 mL), was added (3R,4S)-benzyl 3-amino-4-methoxypyrrolidine-1-carboxylate (enantiopure Intermediate 12, 0.40 g, 1.60 mmol) and N,N-diisopropylethylamine (0.3 mL, 3.1 mmol). The mixture was heated at 85° C. overnight. After cooling, the mixture was added water, stirred for 3 h, filtered, rinsed with water, and dried to give (3R,4S)-benzyl 3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-4-methoxypyrrolidine-1-carboxylate (0.62 g, 87% yield) as a brown solid. MS (ES+) m/z: 487.1, 488.3 (M+H); LC retention time: 3.82 min (analytical HPLC Method).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-9a7f23d0ab9b4296b5e5f29172f7b688
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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