Dimethylamine → HCID 178483679, compound

HRID 449062Notes

Reaction equation

HRID 449062 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].C1COCC1>CO>[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 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 178427762HCID 178427762, compound

Product 1

HCID 178483679HCID 178483679, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of cis-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (30.0 mg, 0.0555 mmol), 2 M of dimethylamine in MeOH (2 mL) and THF (5 mL, 0.06 mol) was heated to 60° C. overnight in a sealed tube. The material was concentrated in vacuo, redissolved in minimal MeOH/DCM, and loaded onto a prep TLC plate, eluting with 6% (7N NH3 in MeOH)/DCM. The band containing the pure product was collected, and the product was filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo, and hexanes was added. The mixture was sonicated until a white precipitate crashed out. The solid was filtered off, washing several times with hexanes, to afford the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ=2.23 (s, 6H), 2.26-2.33 (m, 2H), 2.42 (d, J=6.3 Hz, 2H), 2.57-2.70 (m, 3H), 3.60-3.71 (m, 1H), 5.03 (s, 2H), 7.03-7.17 (m, 7H), 7.34-7.41 (m, 2H), 7.61-7.65 (m, 2H). MS (ES+): m/z 414.19 (100) [MH+]. HPLC: tR=1.98 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe material was concentrated in vacuo
  2. dissolutionredissolved in minimal MeOH/DCM
  3. washeluting with 6% (7N NH3 in MeOH)/DCM
  4. additionThe band containing the pure product
  5. customwas collected
  6. filtrationthe product was filtered off
  7. concentrationThe filtrate was concentrated in vacuo, and hexanes
  8. additionwas added
  9. customThe mixture was sonicated until a white precipitate
  10. filtrationThe solid was filtered off
  11. washwashing several times with hexanes

Sources & evidence

ORD record
ord-0fce6d8e68cb4c0fa590db0d8610dd0d
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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