3-Chlorobenzaldehyde → HCID 59205691, compound

HRID 1409663Notes

Reaction equation

HRID 1409663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.Cl.Cl.[NH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[N:22][CH:21]=[CH:20]2)=[O:15].CCN(C(C)C)C(C)C.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH:23]1[C:24]2[C:19](=[CH:18][C:17]([NH:16][C:14](=[O:15])[CH2:13][NH:12][CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=3)=[CH:26][CH:25]=2)[CH:20]=[CH:21][N:22]=1

Participants

7

Reactant 4

HCID 114773-ChlorobenzaldehydeHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 67300699HCID 67300699, compound

Product 1

HCID 59205691HCID 59205691, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To m-chlorobenzaldehyde in MeOH was added 2-amino-N-(isoquinolin-6-yl)acetamide dihydrochloride (from Example 40) and the pH was adjusted to 5 with DIPEA. The mixture was stirred at room temperature for 2 hours, then NaCNBH3 was added and the pH was adjusted to ˜5.0 with acetic acid. The mixture was stirred 12 hours, quenched with Na2CO3(sat), extracted with EtOAc, dried (Na2SO4), filtered and evaporated to give N-(isoquinolin-6-yl)-2-(3-chlorobenzylamino)acetamide (E59).

Workup

  1. stirringThe mixture was stirred 12 hours
  2. customquenched with Na2CO3(sat)
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6cd90904eb7e4c7d92296118ab891448
Source dataset
uspto-grants-2014_12
Patent number
US08921392B2

Reaction notes

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