Dimethylamine → HCID 69591862, compound

HRID 1795972Notes

Reaction equation

HRID 1795972 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[C:15]([C:18](O)=[O:19])[CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:21]([N:24]([CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C[CH2:56][N:57]=[C:58]=NCCCN(C)C.CNC.CCN(C(C)C)C(C)C>CN(C=O)C>[C:41]([O:40][C:38](=[O:39])[NH:37][CH2:36][CH2:35][CH2:34][N:24]([CH:21]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2=[C:15]([C:18](=[O:19])[N:57]([CH3:58])[CH3:56])[CH:16]=[CH:17][N:11]2[N:10]=1)[CH2:22][CH3:23])[C:25](=[O:33])[C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=1)([CH3:43])([CH3:42])[CH3:44]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22179978HCID 22179978, compound

Product 1

HCID 69591862HCID 69591862, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-benzyl-2-{1-[(3-tert-butoxycarbonylamino-propyl)-(4-methyl-benzoyl)-amino]-propyl}-4-oxo-3,4-dihydro-pyrrolo[2,1-f]-[1,2,4]triazine-5-carboxylic acid (0.0029 g, 0.0048 mmol), HOBt (0.0013 g, 0.0097 mmol), EDCI (0.002 g, 0.0097 mmol), dimethylamine (2 M in THF, 0.024 ml, 0.048 mmol) and DIPEA (0.003 mL, 0.019 mmol) in DMF (0.5 mL) were stirred at room temperature for 16 h. The reaction mixture was concentrated under vacuum, dissolved in EtOAc (3 mL). The organic solution was washed with 10% LiCl (3×2 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 3/1 hexane/EtOAc to afford title compound as a solid (0.001 g, 33%): MS (ESI+) 629 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved in EtOAc (3 mL)
  3. washThe organic solution was washed with 10% LiCl (3×2 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with 3/1 hexane/EtOAc

Sources & evidence

ORD record
ord-245f5d3e53854ad2bb7325dfccf16396
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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