N-(tert-Butoxycarbonyl)-N'-methylethylenediamine → HCID 90463195, compound

HRID 2202112Notes

Reaction equation

HRID 2202112 reaction equation
[CH:1]([C:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH:6]=[N:5][CH:4]=1)=O.[CH3:16][NH:17][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:7]2[C:3]([CH2:1][N:17]([CH3:16])[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:4][N:5]=[CH:6]2)=[CH:9][CH:10]=1)#[N:13]

Participants

5

Reactant 3

HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 90460323HCID 90460323, compound

Product 1

HCID 90463195HCID 90463195, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(5-formyl-1H-imidazol-1-yl)benzonitrile (55 mg, 0.28 mmol, 1.00 equiv) and tert-butyl N-[2-(methylamino)ethyl]carbamate (58 mg, 0.33 mmol, 1.19 equiv) in 1,2-dichloroethane (20 mL) was added NaBH(OAc)3 (178 mg, 0.82 mmol, 2.95 equiv). The reaction was stirred at room temperature for 2 h and then concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-5.4% of methanol in dichloromethane to give 90 mg (91%) of tert-butyl 2-(((1-(4-cyanophenyl)-1H-imidazol-5-yl)methyl)(methyl)amino)ethylcarbamate as a colorless oil. LCMS (method D, ESI): RT=0.98 min, m/z=356.0 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified on a silica gel column
  3. washeluted with 0-5.4% of methanol in dichloromethane

Sources & evidence

ORD record
ord-8eb13eaa78c74a6cabc63489155ebb69
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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