Diisopropylethylamine → HCID 68406051, compound
Reaction equation
[N:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl([O-])(=O)(=O)=O.CN([P+](N(C)C)(N(C)C)Cl)C.C(N(CC)C(C)C)(C)C.[NH2:37][CH2:38][CH2:39][CH2:40][N:41]([C:49]1[S:50][CH:51]=[C:52]([C:54]2[O:55][C:56]3[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=3[CH:58]=2)[N:53]=1)[C:42]([C:44]1[S:45][CH:46]=[CH:47][CH:48]=1)=[O:43]>CN1C(=O)CCC1>[O:55]1[C:56]2[CH:62]=[CH:61][CH:60]=[CH:59][C:57]=2[CH:58]=[C:54]1[C:52]1[N:53]=[C:49]([N:41]([CH2:40][CH2:39][CH2:38][NH:37][C:9](=[O:11])[CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:42]([C:44]2[S:45][CH:46]=[CH:47][CH:48]=2)=[O:43])[S:50][CH:51]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-piperidinepropionic acid (3 mg, 0.02 mmol) and tris(dimethylamino)chlorophosphonium perchlorate (7 mg, 0.02 mmol) was dissolved in NMP (200 μL) followed by the addition of N,N-diisopropylethylamine (17 μL, 0.1 mmol). The reaction mixture was maintained at room temperature for 20 min, then N-(3-aminopropyl)-N-(4-(benzofuran-2-yl)thiazol-2-yl)thiophene-2-carboxamide (7.7 mg, 0.02 mmol) was added, and the reaction mixture was stirred at room temperature overnight. The resulting mixture was subjected to HPLC purification (Method Z) to provide the title compound (3.2 mg) as a pale yellow solid. LC/MS (ESI) m/z 523.5 [M+H]. HPLC retention time (Method C)=3.15 min.
Workup
- customThe resulting mixture was subjected to HPLC purification (Method Z)
Sources & evidence
- ORD record
- ord-f42f7e6708bc4001b65fbf2905f62b13
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07410988B2
Reaction notes
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