Dimethylamine → HCID 178483680, compound

HRID 449065Notes

Reaction equation

HRID 449065 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:24]3[CH2:27][C@H:26]([CH2:28]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:25]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:40][NH:41][CH3:42]>CO.C1COCC1>[CH3:40][N:41]([CH2:28][C@H:26]1[CH2:27][C@H:24]([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]3=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][CH:12]=3)[N:9]=2)[CH2:25]1)[CH3:42]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 178427763HCID 178427763, compound

Product 1

HCID 178483680HCID 178483680, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trans-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (30.0 mg, 0.0555 mmol), dimethylamine in MeOH (2 M, 2 mL) and THF (5 mL) was heated to 60° C. overnight in a sealed tube. The material was concentrated in vacuo, purified by prep TLC (eluting with 5% MeOH in DCM). MS (ES+): m/z 414.19 (100) [MH+]. HPLC: tR=0.65 min (polar—5 min).

Workup

  1. concentrationThe material was concentrated in vacuo
  2. custompurified by prep TLC (eluting with 5% MeOH in DCM)
  3. customHPLC: tR=0.65 min (polar—5 min)

Sources & evidence

ORD record
ord-98af5e0e5c454fd0aceea6fbc2aecb09
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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