Potassium Carbonate → HCID 73855080, compound

HRID 2122003Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH2:7]([N:14]1[C:18](=[O:19])[C:17](=[C:20]2[N:24]([CH3:25])[C:23]3[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:22]=3[S:21]2)[S:16][C:15]1=[N:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[NH:40][CH2:41][CH3:42])[C:35]#[N:36])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:44][C:45]([O:47][CH3:48])=[O:46]>CC(=O)CC>[CH3:48][O:47][C:45](=[O:46])[CH2:44][O:30][C:27]1[CH:28]=[CH:29][C:22]2[S:21][C:20](=[C:17]3[S:16][C:15](=[N:31][C:32]4[CH:33]=[C:34]([C:35]#[N:36])[CH:37]=[CH:38][C:39]=4[NH:40][CH2:41][CH3:42])[N:14]([CH2:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:18]3=[O:19])[N:24]([CH3:25])[C:23]=2[CH:26]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a suspension of K2CO3 (41 mg, 5 equiv) in 2-butanone (2 mL) were added the product of Example 57 (31 mg, 0.06 mmol) and methyl 2-bromoacetate (7 μL, 1.2 equiv). The resulting suspension was heated at 75° C. overnight. After cooling, the reaction mixture was filtered, and the filtrate was evaporated to give a crude material, which was purified by chromatography on silica gel, eluting with MeOH-DCM (0:100 to 3:97) to give the title compound (5 mg). 1H-NMR (CDCl3): δ 7.63 (1H, d), 7.28-7.39 (6H, m), 7.13 (1H, d), 7.08 (1H, d), 6.84 (1H, dd), 6.62 (1H, d), 5.13 (2H, s), 4.98 (1H, t), 4.88 (2H, s), 3.79 (3H, s), 3.68 (3H, s), 3.05 (2H, m), 0.99 (3H, t); MS(ESI): 586 (MH+).

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
customthe filtrate was evaporated
customto give a crude material, which
customwas purified by chromatography on silica gel
washeluting with MeOH-DCM (0:100 to 3:97)

Sources & evidence

ORD record: ord-d16f03577c6d4dc8adbc3239d9d2c045
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696473B2

Reaction notes

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