Diisopropylethylamine → HCID 11176458, compound

HRID 639491Notes

Reaction equation

HRID 639491 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([C:12]([OH:14])=O)[CH:11]=1.C(N(C(C)C)CC)(C)C.[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.[NH2:56][CH2:57][C@@H:58]([OH:60])[CH3:59]>O.CN(C)C=O>[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=2)[CH:9]=[C:10]([C:12]([NH:56][CH2:57][C@@H:58]([OH:60])[CH3:59])=[O:14])[CH:11]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 11267270HCID 11267270, compound

Product 1

HCID 11176458HCID 11176458, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

8-[(2,6-dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid (30 g, 0.0928 mol) and 30 g diisopropylethylamine (30 g, 0.233 mol) were added to dimethylformamide (DM) (250 ml). o-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (36 g, 0.112 mol) was added. The mixture was stirred for 15 min at room temperature. (S)-1-amino-2-propanol (8.4 g, 0.112 mol) was added and the stirring was continued for 1 h at room temperature. Water (100 ml) was added and the reaction mixture was heated to 70° C. The product was precipitated by slowly adding more water (200 ml). The mixture was then stirred for 5 h at 65-70° C. After cooling to room temperature the product was filtered off and washed with 40% methanol solution. 33.7 g of the compound of the invention was obtained.

Workup

  1. waitthe stirring was continued for 1 h at room temperature
  2. temperaturethe reaction mixture was heated to 70° C
  3. customThe product was precipitated
  4. additionby slowly adding more water (200 ml)
  5. stirringThe mixture was then stirred for 5 h at 65-70° C
  6. temperatureAfter cooling to room temperature the product
  7. filtrationwas filtered off
  8. washwashed with 40% methanol solution

Sources & evidence

ORD record
ord-4d733ea077b4480fad7c140e8f4dfb4f
Source dataset
uspto-grants-2010_04
Patent number
US07691875B2

Reaction notes

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