Potassium Carbonate → HCID 178501946, compound

HRID 516213Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:47])=[C:4]([CH:9]([OH:46])[CH2:10][CH2:11][NH:12][C@@H:13]2[C:29]3=[N:30][C:26](=[CH:27][N:28]3COCC[Si](C)(C)C)[C:25]3[C:20](=[CH:21][C:22]([NH:39][C:40](=[O:43])[O:41][CH3:42])=[CH:23][CH:24]=3)[NH:19][C:18](=[O:44])[C@H:17]([CH3:45])[CH2:16][CH2:15][CH2:14]2)[C:5]([F:8])=[CH:6][CH:7]=1.[C:48]([O-])([O-])=[O:49].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:3]([F:47])=[C:4]([C@@H:9]2[O:46][C:48](=[O:49])[N:12]([C@@H:13]3[C:29]4=[N:30][C:26](=[CH:27][NH:28]4)[C:25]4[C:20](=[CH:21][C:22]([NH:39][C:40](=[O:43])[O:41][CH3:42])=[CH:23][CH:24]=4)[NH:19][C:18](=[O:44])[C@H:17]([CH3:45])[CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:10]2)[C:5]([F:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Methyl N-[(10R,14S)-14-{[3-(3-chloro-2,6-difluorophenyl)-3-hydroxypropyl]amino}-10-methyl-9-oxo-16-{[2-(trimethylsilyl)ethoxy]methyl}-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate: A solution of 10F (30 mg, 0.062 mmol), Intermediate 2 (36 mg, 0.108 mmol) and K2CO3 (34.0 mg, 0.246 mmol) in ACN (1 mL) was sealed and heated at 75° C. for 24 h in a 1 dram vial. The reaction mixture was cooled and filtered off the solids. The organic layer is concentrated, dissolved in MeOH and purified by reverse phase HPLC to isolate the desired product as a white solid. The solid was dissolved in MeOH, passed through HCO3 resin cartridge and concentrated to get the desired product (26 mg, 61%, free base) as a white solid. MS (ESI) m/z: 692.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered off the solids
concentrationThe organic layer is concentrated
dissolutiondissolved in MeOH
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-df1a11cceb7a4f11b8f5fe14e73806b3
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108981B2

Reaction notes

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