Acetic Acid → HCID 71736757, compound

HRID 717087Notes

Reaction equation

HRID 717087 reaction equation
[C:1](O)(=[O:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:36][C:37]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:38]=1[CH:39]=[C:40]([C:48]1[CH:53]=[CH:52][C:51]([CH2:54][N:55]3[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]3)=[CH:50][CH:49]=1)[NH:41][C:42]2=[O:47]>C(Cl)Cl>[C:1]([N:58]1[CH2:59][CH2:60][N:55]([CH2:54][C:51]2[CH:50]=[CH:49][C:48]([C:40]3[NH:41][C:42](=[O:47])[C:43]4[C:38]([CH:39]=3)=[C:37]([CH3:36])[CH:46]=[CH:45][CH:44]=4)=[CH:53][CH:52]=2)[CH2:56][CH2:57]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 71737385HCID 71737385, compound

Product 1

HCID 71736757HCID 71736757, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of acetic acid (0.005 mL, 0.068 mmol) in CH2Cl2 (5 mL) was added TBTU (22 mg, 0.068 mmol) and N,N-diisopropylethylamine (0.036 mL, 0.20 mmol) and the reaction stirred for 10 min at RT. 5-Methyl-3-(4-piperazin-1-ylmethylphenyl)-2H-isoquinolin-1-one (23 mg, 0.068 mmol) was then added and the reaction stirred for 2 h at RT. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC-MS to afford 3-[4-(4-acetyl-piperazine-1-ylmethyl)-phenyl]-5-methyl-2H-isoquinolin-1-one as a white solid (2 mg, 9%).

Workup

  1. stirringthe reaction stirred for 2 h at RT
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-7d41b0d4b8fd422fb1cebacc07a29c20
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

Loading…