Triethylamine → HCID 24989647, compound

HRID 552395Notes

Reaction equation

HRID 552395 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:16]4[CH:17]=[CH:18][N:19]=[C:15]4[C:14]([NH:20][C:21]4[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=4)=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[CH3:30][N:31](C)[C:32]1C=CC(CN)=C[CH:33]=1.[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH3:42].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=C[C:58]=2N=N1>CN(C)C=O.CCOC(C)=O>[N:43]1([CH:46]2[CH2:33][CH2:32][N:31]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:14]4[C:15]5[N:16]([CH:17]=[CH:18][N:19]=5)[C:11]([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[C:2](=[O:1])[NH:3][CH2:4]6)=[CH:12][CH:13]=4)=[CH:29][CH:28]=3)=[O:26])[CH2:30][CH2:47]2)[CH2:44][CH2:45][CH2:58][CH2:42][CH2:41]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 808264-(Aminomethyl)-N,N-dimethylanilineHCID 2724699PyBOPHCID 57580695HCID 57580695, compound

Product 1

HCID 24989647HCID 24989647, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid (37.0 mg, 0.096 mmol), 4-dimethylaminobenzylamine (15.91 mg, 0.106 mmol) and triethylamine (10.72 mg, 0.047 mL, 0.106 mmol) in dimethylformamide (0.4 mL) under nitrogen is added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (55.10 mg, 0.106 mmol). The reaction mixture is then stirred at room temperature for 18 hours. The mixture is then diluted with EtOAc and washed with saturated aqueous NaHCO3. The combined organic layers are dried (MgSO4) and the solvent is removed under reduced. The crude product is purified by reverse phase HPLC to yield the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. customthe solvent is removed
  4. customThe crude product is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-dc7734a89d844ac084dc0fa1c71483da
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

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