Diisopropylethylamine → {(2S)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-2-yl}methanol

HRID 925604Notes

Reaction equation

HRID 925604 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16](Cl)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.C(N(C(C)C)CC)(C)C.[NH:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][OH:35]>C(O)CCC.CN1C(=O)CCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([N:29]3[CH2:33][CH2:32][CH2:31][C@H:30]3[CH2:34][OH:35])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 640091L-Prolinol3×HCID 71491928HCID 71491928, compound

Product 1

HCID 71144743{(2S)-1-[3-(1-Benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]pyrrolidin-2-yl}methanol

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent3×

Conditions

Temperature
120 °C

Procedure

To a mixture of 40.5 mg (0.15 mmol) 3-(1-benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine and 25 mg (0.195 mmol) diisopropylethylamine in 1 mL of 1-butanol were added 21 mg (0.22 mmol) (2S)-pyrrolidin-2-ylmethanol in 0.3 mL NMP. The mixture is stirred at 120° C. for 8 h. 16 mg (0.16 mmol) (2S)-pyrrolidin-2-ylmethanol in 0.2 mL NMP were added and shaking at 120° C. was continued for 8 h. Again, 16 mg (0.16 mmol) (2S)-pyrrolidin-2-ylmethanol in 0.2 mL NMP were added and shaking at 120° C. was continued for 8 h.

Workup

  1. stirringshaking at 120° C.
  2. waitwas continued for 8 h
  3. stirringshaking at 120° C.
  4. waitwas continued for 8 h.

Sources & evidence

ORD record
ord-8c6a72f0505a4930ad398d31e1041c49
Source dataset
uspto-grants-2016_03
Patent number
US09284319B2

Reaction notes

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