N,N-Dimethylethylenediamine → HCID 68183349, compound

HRID 513702Notes

Reaction equation

HRID 513702 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:23]=[CH:22][C:21]([CH:24]2[C:37]3[CH:36]=[CH:35][C:34]4[C:29](=[N:30][CH:31]=[CH:32][CH:33]=4)[C:28]=3[NH:27][S:26](=[O:39])(=[O:38])[N:25]2[CH3:40])=[CH:20][C:17]=1[CH:18]=O.[CH3:41][N:42]([CH3:46])[CH2:43][CH2:44][NH2:45]>ClCCCl>[F:15][C:16]1[CH:23]=[CH:22][C:21]([CH:24]2[C:37]3[CH:36]=[CH:35][C:34]4[C:29](=[N:30][CH:31]=[CH:32][CH:33]=4)[C:28]=3[NH:27][S:26](=[O:39])(=[O:38])[N:25]2[CH3:40])=[CH:20][C:17]=1[CH2:18][NH:45][CH2:44][CH2:43][N:42]([CH3:46])[CH3:41]

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 88861907HCID 88861907, compound

Product 1

HCID 68183349HCID 68183349, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added to a solution of 2-fluoro-5-(2-methyl-3,3-dioxo-1,2,3,4-tetrahydro-3λ*6*-thia-2,4,5-triaza-phenanthren-1-yl)-benzaldehyde 422 (50 mg, 0.13 mmol) and N,N-dimethylethane-1,2-diamine (12.9 μl, 0.16 mmol) in DCE (2 ml) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with sat. NaHCO3 solution (1 ml) and the mixture was extracted with EtOAc (5 ml). The organic phase was concentrated in vacuo. The crude residue was triturated from chloroform/MeOH to give the title compound (20 mg, 34%).

Workup

  1. customThe reaction was quenched with sat. NaHCO3 solution (1 ml)
  2. extractionthe mixture was extracted with EtOAc (5 ml)
  3. concentrationThe organic phase was concentrated in vacuo
  4. customThe crude residue was triturated from chloroform/MeOH

Sources & evidence

ORD record
ord-5a5e6429132149e3b3317d4e75616d9a
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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