Water → 6-bromo-4-((1S,2S)-2-hydroxy-2-methylcyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408957Notes

Reaction equation

HRID 1408957 reaction equation
C[C:2]1(C)CCC[C@H:3]1[NH2:7].[BrH:9].[NH2:10][C@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@:12]1([CH3:18])[OH:17].CC[N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])C.O.C[N:30]([CH:32]=[O:33])C>>[Br:9][C:24]1[CH:27]=[C:25]2[C:26]([NH:10][C@H:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C@@:12]3([OH:17])[CH3:18])=[C:2]([C:32]([NH2:30])=[O:33])[CH:3]=[N:7][N:21]2[CH:22]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 15196533(1R)-2,2-dimethylcyclopentan-1-amineHCID 86707707(+/-)-(1S,2S)-2-amino-1-methylcyclohexanolhydrobromide

Product 1

HCID 682918326-bromo-4-((1S,2S)-2-hydroxy-2-methylcyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 57%

Conditions

Temperature
90 °C

Procedure

A mixture of Preparation 5 (41.8 mg, 0.152 mmol) and (±)-(1S,2S)-2-amino-1-methylcyclohexanol hydrobromide (32 mg, 0.152 mmol) in DMF (0.4 mL) was added DIPEA (0.08 mL, 0.46 mmol) and the mixture was heated to 90° C. for 18 h. The reaction was cooled to rt and added water (3 mL) then stirred rapidly for 3 h and filtered. The solids were purified on silica gel (100% heptane to 50% ethyl acetate/heptane to 100% ethyl acetate) to afford the title compound (31.6 mg, 57% yield). LCMS 369.05 (M+2)+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationfiltered
  3. customThe solids were purified on silica gel (100% heptane to 50% ethyl acetate/heptane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-352baef288554980943518082273199b
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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