Azetidine → HCID 131733329, compound

HRID 516169Notes

Reaction equation

HRID 516169 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)=[CH:9][N:8]([CH:23]3[CH2:26][N:25]([C:27](=[O:32])[CH:28]=[CH:29][CH2:30]Br)[CH2:24]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:33]1[CH2:36][CH2:35][CH2:34]1>C1COCC1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)=[CH:9][N:8]([CH:23]3[CH2:26][N:25]([C:27](=[O:32])[CH:28]=[CH:29][CH2:30][N:33]4[CH2:36][CH2:35][CH2:34]4)[CH2:24]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 131733330HCID 131733330, compound

Product 1

HCID 131733329HCID 131733329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude product of 1-(3-(4-amino-5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)azetidin-1-yl)-4-bromobut-2-en-1-one (10 mg) obtained in Step 1 above was suspended in THF (0.5 ml). Azetidine (7 μl) was added thereto, and the resulting mixture was stirred for 1 hour at room temperature. After concentrating under reduced pressure, the resulting residue was purified by reversed-phase HPLC purification (water/acetonitrile (0.1% formic acid)) to obtain the title compound as a colorless, amorphous substance (1.6 mg). Table 1 shows the physical properties thereof.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe resulting residue was purified by reversed-phase HPLC purification (water/acetonitrile (0.1% formic acid))

Sources & evidence

ORD record
ord-cba6421754dd4b32abfca43cf6e132a6
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

Loading…