Ammonium Hydroxide → tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate

HRID 578713Notes

Reaction equation

HRID 578713 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][C:15]2[C:24]3[C:19](=[C:20]([C:26]([O:28]C)=O)[CH:21]=[C:22]([I:25])[CH:23]=3)[N:18]=[CH:17][N:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[NH4+:31]>CC(O)C.CS(C)=O.O>[NH2:31][C:26]([C:20]1[CH:21]=[C:22]([I:25])[CH:23]=[C:24]2[C:19]=1[N:18]=[CH:17][N:16]=[C:15]2[NH:14][C@H:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:28]

Participants

6

Reactant 2

HCID 14923Ammonium HydroxideHCID 66763868methyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]amino}-6-iodoquinazoline-8-carboxylate

Product 1

HCID 66762696tert-butyl (3S)-3-{[8-(aminocarbonyl)-6-iodoquinazolin-4-yl]amino}piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Dissolved methyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]amino}-6-iodoquinazoline-8-carboxylate (380.00 mg; 0.74 mmol; 1.00 eq.) in iPrOH (2.00 ml) and DMSO (2.00 ml) and then added ammonium hydroxide (5.00 ml). Stirred mixture at room temperature for 2.5 days. LCMS: M+1=498 major peak. Partially concentrated reaction. Diluted with water and filtered the resulting solids. Washed with water and dried to give an off-white solid (110 mg). LCMS: M+1=498.

Workup

  1. customPartially concentrated reaction
  2. filtrationfiltered the resulting solids
  3. washWashed with water
  4. customdried

Sources & evidence

ORD record
ord-aea7d097eb3d452ba2be658fb18f28b3
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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