Potassium Carbonate → (1aR,3aR,5S,7aR,15aS,Z)-methyl 5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

HRID 926011Notes

Reaction equation

BrC1C=CC(S([O:11][C@@H:12]2[CH2:37][CH2:36][C@H:15]3[C:16](=[O:35])[N:17]([CH3:34])[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][C@@H:24]4[CH2:29][C@@:25]4([C:30]([O:32][CH3:33])=[O:31])[NH:26][C:27](=[O:28])[C@@H:14]3[CH2:13]2)(=O)=O)=CC=1.[C:38]([C:40]1[N:41]=[C:42]([C:45]2[CH:54]=[C:53](O)[C:52]3[C:47](=[C:48]([CH3:58])[C:49]([O:56][CH3:57])=[CH:50][CH:51]=3)[N:46]=2)[S:43][CH:44]=1)#[CH:39].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[C:38]([C:40]1[N:41]=[C:42]([C:45]2[CH:54]=[C:53]([O:11][C@H:12]3[CH2:37][CH2:36][C@H:15]4[C:16](=[O:35])[N:17]([CH3:34])[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH:23][C@@H:24]5[CH2:29][C@@:25]5([C:30]([O:32][CH3:33])=[O:31])[NH:26][C:27](=[O:28])[C@@H:14]4[CH2:13]3)[C:52]3[C:47](=[C:48]([CH3:58])[C:49]([O:56][CH3:57])=[CH:50][CH:51]=3)[N:46]=2)[S:43][CH:44]=1)#[CH:39]

Participants

Conditions

Temperature: 70 °C

Procedure

Compound 44 (0.13 mmol) and 2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-ol (0.14 mmol) 209b were dissolved in NMP (0.5 mL). K2CO3 (0.19 mmol) was added and the reaction mixture was heated at 70° C. for 2 days. The crude material was purified by silica gel chromatography (PE/EtOAc) to yield compound 45 as a beige solid. MS (ESI, EI+): m/z=657 (MH+).

Workup

customThe crude material was purified by silica gel chromatography (PE/EtOAc)

Sources & evidence

ORD record: ord-aa5f953bbdd749978f33f011820b326d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284307B2

Reaction notes

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