Water → HCID 68291190, compound

HRID 1408950Notes

Reaction equation

HRID 1408950 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.[OH:15][C:16]12[CH2:26][CH:20]3[CH2:21][C:22]([OH:25])([CH2:24][C:18]([NH2:27])([CH2:19]3)[CH2:17]1)[CH2:23]2.CCN(C(C)C)C(C)C.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:27][C:18]34[CH2:24][C:22]5([OH:25])[CH2:21][CH:20]([CH2:26][C:16]([OH:15])([CH2:23]5)[CH2:17]3)[CH2:19]4)=[C:8]([C:11]([NH2:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 22463559HCID 22463559, compoundHCID 682911926-Bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291190HCID 68291190, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 80 mg, 0.291 mmol), 3,5-dihydroxyadamantan-1-amine (53.4 mg, 0.291 mmol) and DIPEA (0.104 mL, 0.583 mmol) in DMF (1 mL) was heated in microwave oven at 130° C. for 1.5 h. The reaction mixture was cooled to rt, water added (4 volumes) and the resulting mixture was stirred rapidly overnight. The solids were filtered and rinsed with water to afford the title compound as a yellow solid (72 mg, 56% yield). HPLC (condition 0): retention time=2.16 min; LCMS: 423.00 (M+2); 1H NMR (CDCl3, 400 MHz) δ 7.95 (s, 1H), 7.65 (d, J=1.7 Hz, 1H), 7.01 (d, J=1.8 Hz, 1H), 6.23 (s, 2H), 2.52 (m, 1H), 2.14 (app dd, J=7.1 Hz, 4H), 2.01 (m, 2H), 1.82 (m, 2H), 1.72 (s, 4H).

Workup

  1. filtrationThe solids were filtered
  2. washrinsed with water

Sources & evidence

ORD record
ord-4c326acee2c041e6989d16cb77d0628a
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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