Acetic Acid → HCID 89442445, compound

HRID 632723Notes

Reaction equation

HRID 632723 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:20])=[N:10][CH:11]=[N:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:29]([Cl:30])=[CH:28][C:25]([CH:26]=O)=[C:24]([OH:31])[CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[NH2:20][C:9]1[N:10]=[CH:11][N:12]=[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:26][C:25]3[CH:28]=[C:29]([Cl:30])[C:22]([Cl:21])=[CH:23][C:24]=3[OH:31])[CH2:16][CH2:15]2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5283894,5-dichloro-2-hydroxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 89442443HCID 89442443, compound

Product 1

HCID 89442445HCID 89442445, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of 5-(4-fluoro-phenyl)-6-piperazin-1-yl-pyrimidin-4-ylamine (400.0 mg; 1.46 mmol; 1.00 eq.), 4,5-dichloro-2-hydroxy-benzaldehyde (279.5 mg; 1.46 mmol; 1.00 eq.), Acetic acid (87.8 mg; 1.46 mmol; 1.00 eq.) and sodium triacetoxy borohydride (926.1 mg; 4.39 mmol; 3.00 eq.) in DCE (10 ml) was stirred overnight at RT. The reaction solution was diluted with DCM and washed with brine. The organic layer was dried and concentrated, which was added 10 ml of ether and stirred for 5 mins. The precipitate was filtered to afford the title as white off solid (528 mg, yield 80.5%). LC-MS: (M+1=448, obsd.=448/450).

Workup

  1. washwashed with brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. additionwhich was added 10 ml of ether
  5. stirringstirred for 5 mins
  6. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-a2798236ce7f480fbef594c7cd7ffd66
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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