N,N-Dimethylethylenediamine → HCID 44208456, compound

HRID 1029267Notes

Reaction equation

HRID 1029267 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[CH:26]=[CH:25][N:24]=[C:23]3[C:18]=2[C:19]2[C:20](=[C:28]([C:32]([OH:34])=O)[CH:29]=[CH:30][CH:31]=2)[C:21](=[O:27])[NH:22]3)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:35]1[N:39]=[CH:38][N:37]([C:40](N2C=NC=C2)=O)[CH:36]=1.CN(C)CCN>CN(C=O)C.O>[CH3:38][N:37]([CH3:40])[CH2:36][CH2:35][NH:39][C:32]([C:28]1[CH:29]=[CH:30][CH:31]=[C:19]2[C:18]3[C:23](=[N:24][CH:25]=[CH:26][C:17]=3[NH:16][C:13]3[CH:12]=[CH:11][C:10]([NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:15][CH:14]=3)[NH:22][C:21](=[O:27])[C:20]=12)=[O:34]

Participants

6

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 58168164HCID 58168164, compound

Product 1

HCID 44208456HCID 44208456, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

434 (20 mg, 0.04 mmol), and CDI (14 mg, 0.09 mmol) were suspended in DMF (1 mL), and stirred for 2 h. N,N-dimethylethane-1,2-diamine (8 mg, 0.09 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with H2O. The resulting precipitate was filtered, washed with MeOH, and dried under vacuum to provide 435. LC-MS (M+H=521, obsd.=521). 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 6H), 2.49 (4H), 6.93 (d, 1H), 7.20 (d, 2H), 7.54 (m, 3H), 7.76 (m, 3H), 7.97 (d, 1H), 8.10 (d, 1H), 8.27 (s, 1H), 8.85 (d, 1H), 9.18 (s, 1H), 10.27 (s, 1H).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with MeOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9a88737ca6ce43739e654e9f49303b4c
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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