Formaldehyde → HCID 178434263, compound

HRID 490106Notes

Reaction equation

HRID 490106 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][CH:14]=[C:15]([N:17]4[CH2:22][CH2:21][NH:20][C@@H:19]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:18]4)[N:16]=3)[CH:9]=2)[NH:4][N:3]=1.C=O.[C:32]([BH3-])#N>C(O)(=O)C>[CH2:23]([C@@H:19]1[N:20]([CH3:32])[CH2:21][CH2:22][N:17]([C:15]2[N:16]=[C:11]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[NH:4][N:3]=[C:2]4[CH3:1])[N:12]=[N:13][CH:14]=2)[CH2:18]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 498716Cyano-borohydrideHCID 178434266HCID 178434266, compound

Product 1

HCID 178434263HCID 178434263, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-[(S)-3-benzylpiperazin-1-yl]-3-(3-methylindazol-5-yl)-[1,2,4]triazine 12 (14 mg, 0.036 mmol.) in 10% methanolic acetic acid was added 37% aqueous formaldehyde solution (0.06 mL, 0.74 mmol.) and cyanoborohydride resin (2.42 equiv./g, 44 mg, 0.11 mmol.). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 5-[(S)-3-benzyl-4-methyl-piperazin-1-yl]-3-(3-methylindazol-5-yl)-[1,2,4]triazine 28 (7.1 mg, 0.018 mmol.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-8cad9c04f02b473c9a91a946fd7604a3
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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