Dimethylamine → HCID 69106354, compound

HRID 2053039Notes

Reaction equation

HRID 2053039 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:12]1[C:13]2[N:14]([C:21]([CH3:25])=[C:22]([CH3:24])[N:23]=2)[CH:15]=[C:16]([C:18](O)=[O:19])[CH:17]=1.F[B-](F)(F)F.N1(O[C:41](N(C)C)=[N+:42](C)[CH3:43])C2C=CC=CC=2N=N1.CNC.C(=O)([O-])O.[Na+]>ClCCl>[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][C:12]1[C:13]2[N:14]([C:21]([CH3:25])=[C:22]([CH3:24])[N:23]=2)[CH:15]=[C:16]([C:18]([N:42]([CH3:43])[CH3:41])=[O:19])[CH:17]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69114052HCID 69114052, compound

Product 1

HCID 69106354HCID 69106354, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 g (5.7 mmol) 8-(trans-2,3-dihydro-2-hydroxy-1-indenyloxy)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylic acid and 2.4 g (7.4 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) are suspended in 100 ml dichloromethane and 2.1 ml (11.4 mmol) dimethylamine (5.6 M in ethanol) are added to the reaction mixture. After stirring for 3 h at room temperature, the reaction mixture is hydrolyzed with saturated aqueous sodium hydrogen carbonate. The organic phase is separated and the aqueous layer is extracted with dichloromethane The combined organic phases are dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) and crystallization from methanol/light petroleum ether yields 1.18 g (57%) of the title compound as a colourless solid (m.p. 182-184° C.).

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous layer is extracted with dichloromethane The combined organic phases
  3. dry with materialare dried over anhydrous magnesium sulphate
  4. customevaporated
  5. customPurification of the residue by column chromatography on silica gel
  6. customdichloromethane:methanol (20:1) and crystallization from methanol/light petroleum ether

Sources & evidence

ORD record
ord-a72902cdaa7d4103925de3aa563a8f16
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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