Dimethylamine → HCID 178483678, compound

HRID 2373898Notes

Reaction equation

HRID 2373898 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:25]3[CH2:28][C@H:27]([CH2:29]OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:26]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:41][NH:42][CH3:43]>C1COCC1>[CH3:41][N:42]([CH2:29][C@@H:27]1[CH2:26][C@H:25]([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][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)[N:9]=2)[CH2:28]1)[CH3:43]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178427761HCID 178427761, compound

Product 1

HCID 178483678HCID 178483678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A sealed tube containing a solution of cis-toluene-4-sulfonic acid 3-[8-amino-1-(3-benzyloxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]cyclobutylmethyl ester (100 mg, 0.18 mmol) in THF (3 mL) was charged with dimethylamine solution (1.8 mL, 3.6 mmol, 2.0 M in THF), sealed, and heated at 50° C. overnight. The mixture was concentrated and the residue was diluted with ethyl acetate (40 mL), washed with sat. aq. NaHCO3 (2×15 mL) and brine (2×15 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was recrystallized to afford a white solid; LC-MS (ES, Pos.): m/z 428 [MH+]; 1H NMR (CDCl3, 400 MHz) δ 2.23 (s, 6H), 2.24-2.32 (m, 2H), 2.42 (d, J=6.1 Hz, 2H), 2.61-2.69 (m, 3H), 3.64 (m, 1H), 4.98 (br s, 2H, NH2), 5.15 (s, 2H), 7.00-7.04 (m, 2H), 7.12 (d, J=5.0 Hz, 1H), 7.23-7.27 (m, 2H), 7.31-7.46 (m, 6H).

Workup

  1. customsealed
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with ethyl acetate (40 mL)
  4. washwashed with sat. aq. NaHCO3 (2×15 mL) and brine (2×15 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was recrystallized
  8. customto afford a white solid

Sources & evidence

ORD record
ord-8cdba1bca5fb43dbb9684a802510efee
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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