6-Chloro-4-morpholinopyridazin-3-amine → tert-Butyl 3-(6-chloro-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

HRID 718589Notes

Reaction equation

HRID 718589 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)=O.[Cl:16][C:17]1[N:22]=[N:21][C:20]([NH2:23])=[C:19]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:18]=1>CN(C=O)C>[Cl:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:20]2[N:21]([CH:2]=[C:3]([CH:5]3[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]3)[N:23]=2)[N:22]=1

Participants

4

Reactant 2

HCID 575175366-Chloro-4-morpholinopyridazin-3-amineHCID 90357297Tert-butyl 3-(2-bromoacetyl)azetidine-1-carboxylate

Product 1

HCID 117732465tert-Butyl 3-(6-chloro-8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyl 3-(2-bromoacetyl)azetidine-1-carboxylate (207 mg, 0.744 mmol) in DMF (1 mL) was added to a solution of compound 19a (99.8 mg, 0.465 mmol) and Na2HPO4 (165 mg, 2.50 mmol) in DMF (20 mL). The resulting mixture was stirred at rt overnight. The reaction mixture was concentrated in vacuo and the residue obtained was purified by normal phase column chromatography on silica gel (0-100% EtOAc/heptane) to obtain compound 19b. Mass Spectrum (LCMS, ESI pos.): Calcd. for C19H25ClN4O3: 393.2 (M+H). found: 393.3.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified by normal phase column chromatography on silica gel (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-3f47937894774e39a9314f640b2a8eef
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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