Sodium Carbonate → HCID 67050608, compound
Reaction equation
C([O:4][CH2:5][CH2:6][NH:7][C:8](=[O:35])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([N:16]([CH3:34])[C:17]([C:19]2[S:33][C:22]3[C:23]4[CH:31]=[CH:30][C:29](Br)=[CH:28][C:24]=4[O:25][CH2:26][CH2:27][C:21]=3[CH:20]=2)=[O:18])[CH:10]=1)(=O)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:57][C:39]2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH3:78][S:79]([CH2:82][CH2:83][NH2:84])(=[O:81])=[O:80].Cl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:8](=[O:35])[NH:7][CH2:6][CH2:5][OH:4])=[CH:10][C:11]=1[N:16]([CH3:34])[C:17]([C:19]1[S:33][C:22]2[C:23]3[CH:31]=[CH:30][C:29]([C:39]([NH:84][CH2:83][CH2:82][S:79]([CH3:78])(=[O:81])=[O:80])=[O:57])=[CH:28][C:24]=3[O:25][CH2:26][CH2:27][C:21]=2[CH:20]=1)=[O:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 2-(3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzamido)ethyl acetate (400 mg, 0.69 mmol), Pd(OAc)2 (10 mg, 0.045 mmol), Xantphos (40 mg, 0.069 mmol), MeSO2CH2CH2NH2.HCl (165 mg, 1.04 mmol) and Na2CO3 (219 mg, 2.07 mmol) in toluene (5 mL) was heated at 80° C. under atmosphere of CO from balloon overnight. Then it was filtrated and concentrated, the crude product was purified by column (EtOAc:MeOH=10:1) to afford 385 (76.8 mg, yield: 18%). 1HNMR (DMSO-d6, 400 MHz): δ8.70 (t, J=5.6 Hz, 1H), 8.61 (d, J=5.6 Hz, 1H), 8.07-7.41 (m, 6H), 6.57 (s, 1H), 4.72 (s, 1H), 4.71 (t, J=5.6 Hz, 1H), 3.63-2.95 (m, 16H). LC-MS: (ESI, m/z)=606 [M+H]+
Workup
- filtrationThen it was filtrated
- concentrationconcentrated
- customthe crude product was purified by column (EtOAc:MeOH=10:1)
Sources & evidence
- ORD record
- ord-ea29449e91d243eaad0620bd964c0b73
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175009B2
Reaction notes
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