Triethylamine → HCID 16656846, compound

HRID 1009180Notes

Reaction equation

HRID 1009180 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][N:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][C:10]2=[O:23])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:24][CH2:25][C:26](O)=[O:27].CN(C(O[N:37]1N=NC2C=[CH:41][CH:42]=[CH:43][C:38]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCCC1.C(N(CC)CC)C>CN(C)C=O>[CH3:1][C:2]1[C:3]([NH:24][CH2:25][C:26](=[O:27])[N:37]2[CH2:38][CH2:43][CH2:42][CH2:41]2)=[CH:4][CH:5]=[CH:6][C:7]=1[CH2:8][N:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:11][C:10]1=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67306209HCID 67306209, compound

Product 1

HCID 16656846HCID 16656846, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {2-Methyl-3-[2-oxo-4-(2-thiophen-2-yl-ethoxy)-2H-pyridin-1-ylmethyl]-phenylamino}-acetic acid (50 mg, 0.13 mmol), TBTU (60 mg, 0.19 mmol), pyrrolidine (0.02 ml, 0.25 mmol) and triethylamine (0.09 ml, 0.63 mmol) was dissolved in N,N-dimethylformamide (0.5 ml) and stirred at room temperature. After 1 hour, the resulting solution was evaporated, extracted with dichloromethane (20 ml) and subjected to silica gel column chromatography (ethyl acetate/MeOH, 20:1) to obtain the titled compound (41 mg, 71%).

Workup

  1. customthe resulting solution was evaporated
  2. extractionextracted with dichloromethane (20 ml)

Sources & evidence

ORD record
ord-5bdaf45d26f64c90baf2a1ab3ee4c880
Source dataset
uspto-grants-2011_07
Patent number
US07973060B2

Reaction notes

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