Triethylamine → HCID 69202029, compound
Reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[C:37]([OH:39])=O.C(N(CC)CC)C.Cl.[NH2:48][C:49]1([C:55]#[C:56][C:57]2[CH:66]=[CH:65][C:60]([C:61]([O:63][CH3:64])=[O:62])=[CH:59][CH:58]=2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>CN(C=O)C.C(OCC)(=O)C>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[C:37]([NH:48][C:49]1([C:55]#[C:56][C:57]2[CH:58]=[CH:59][C:60]([C:61]([O:63][CH3:64])=[O:62])=[CH:65][CH:66]=2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1)=[O:39]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP, 249 mg, 0.51 mmol) and indole-2-carboxylic acid (83 mg, 0.51 mmol) in DMF (5 ml) was treated with triethylamine (0.21 ml, 1.5 mmol). After 20 min, methyl 4-(1-amino-cyclohex-1-yl-ethynyl)-benzoate hydrochloride (150 mg, 0.51 mmol) was added and the reaction mixture was stirred for additional 16 h. The reaction mixture was diluted with ethyl acetate (50 ml) and the organic layer was washed with water (25 ml), 1M aqueous HCl (25 ml), saturated sodium bicarbonate (25 ml), and brine, dried over sodium sulfate, and concentrated in vacuo to provide crude methyl 4-[1-(1H-indol-2-yl-carbonylamino)-cyclohex-1-yl-ethynyl]-benzoate which was used without further purification.
Workup
- washthe organic layer was washed with water (25 ml), 1M aqueous HCl (25 ml), saturated sodium bicarbonate (25 ml), and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fe9444a98f334fdaa655f8cd092e9d3b
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368572B2
Reaction notes
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