Diisopropylethylamine → HCID 58046371, compound

HRID 1035795Notes

Reaction equation

HRID 1035795 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[N:24]([S:27]([C:30]5[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=5)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=34)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.Cl.[CH2:38]1[C:43]2([CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH2:42][CH2:41][CH2:40][N:39]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50].C(N(C(C)C)CC)(C)C>C(O)CCCC>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([N:46]4[CH2:45][CH2:44][C:43]5([CH2:38][N:39]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[CH2:40][CH2:41][CH2:42]5)[CH2:48][CH2:47]4)=[N:7][N:6]3[C:8]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[N:24]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:29])=[O:28])[CH:25]=[CH:26][C:19]=23)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58046364HCID 58046364, compoundHCID 66570708tert-Butyl 2,9-diazaspiro[5.5]undecane-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 58046371HCID 58046371, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 0.15 g (0.29 mmol) of 6-chloro-2-(4-fluorophenyl)-3-[1-(4-methylphenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazine, prepared according to the method described in step 3.2 of Example 3, 0.337 g (1.15 mmol) of tert-butyl 2,9-diazaspiro[5.5]undecane-2-carboxylate hydrochloride (1:1) (CAS 1023301-88-3) and 0.224 g (1.7 mmol) of diisopropylethylamine in 2 ml of pentanol is heated under reflux for 40 hours at 140° C. The solvent is then evaporated under reduced pressure and the residue is purified by chromatography on a silica gel column by eluting with a gradient of dichloromethane, methanol and aqueous ammonia (of 100/0/0 to 90/10/1) in order to give 0.190 mg of tert-butyl 9-{2-(4-fluorophenyl)-3-[1-(4-methylphenylsulphonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazo[1,2-b]pyridazin-6-yl}-2,9-diazaspiro[5.5]undecane-2-carboxylate after crystallization in methanol.

Workup

  1. customprepared
  2. temperatureis heated
  3. customThe solvent is then evaporated under reduced pressure
  4. customthe residue is purified by chromatography on a silica gel column
  5. washby eluting with a gradient of dichloromethane, methanol and aqueous ammonia (of 100/0/0 to 90/10/1) in order

Sources & evidence

ORD record
ord-8e4a1873c40e44cf89b86c168081986c
Source dataset
uspto-grants-2013_10
Patent number
US08546395B2

Reaction notes

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