Diisopropylethylamine → HCID 66622465, compound

HRID 340945Notes

Reaction equation

HRID 340945 reaction equation
[Cl:1][C:2]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][NH:5][C:6](=[O:29])[N:7]([CH:9]([CH2:25][CH2:26][CH:27]=O)[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8].[CH3:35]CN(C(C)C)C(C)C.Cl.N1[C:49]2[NH:50][CH2:51][CH2:52][NH:53][C:48]=2[N:47]=[N:46]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:1][C:2]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:3]=1[CH2:4][NH:5][C:6](=[O:29])[N:7]([CH:9]([CH2:25][CH2:26][CH2:27][N:50]1[CH2:51][CH2:52][N:53]2[CH:35]=[N:46][N:47]=[C:48]2[CH2:49]1)[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 76654753HCID 76654753, compoundHCID 178420749HCID 178420749, compound

Product 1

HCID 66622465HCID 66622465, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-5-oxo-pentyl ester (75 mg crude mixture, 0.15 mmol) in anhydrous DCE (2 mL) and DIEA (56 uL, 0.32 mmol) was added the triazolopiperazine HCl salt (27 mg, 0.17 mmol) at RT. After 5 min of stirring at RT, sodium triacetoxyborohydride (98 mg, 0.45 mmol) was added in one portion. The slurry was stirred for 16 h at RT, the diluted in CH2Cl2 and washed with saturated aq. NaHCO3 and brine. After drying the solution over Na2SO4, the reaction mixture was concentrated and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-5-(5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-pentyl ester (30 mg, 30%) LRMS (M+H+) m/z 595.2.

Workup

  1. stirringThe slurry was stirred for 16 h at RT
  2. washwashed with saturated aq. NaHCO3 and brine
  3. dry with materialAfter drying the solution over Na2SO4
  4. concentrationthe reaction mixture was concentrated
  5. customthe resulting residue was purified on RP-HPLC
  6. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-845d8e5b95d24d3ca4548e6265a6ae21
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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