Ethyl Acetate → LY 393558

HRID 2268787Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[CH2:9][C:8]2[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:7]=2[NH:6][S:5]1(=[O:19])=[O:18])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:39][C:40]1[CH:48]=[C:47]2[C:43]([C:44]([C:49]3[CH2:50][CH2:51][N:52]([CH2:55][CH2:56]O)[CH2:53][CH:54]=3)=[CH:45][NH:46]2)=[CH:42][CH:41]=1.C(OCC)(=O)C>CN(C=O)C.O>[F:39][C:40]1[CH:48]=[C:47]2[C:43]([C:44]([C:49]3[CH2:50][CH2:51][N:52]([CH2:55][CH2:56][N:6]4[C:7]5[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:15])=[O:16])=[CH:10][C:8]=5[CH2:9][N:4]([CH:2]([CH3:1])[CH3:3])[S:5]4(=[O:19])=[O:18])[CH2:53][CH:54]=3)=[CH:45][NH:46]2)=[CH:42][CH:41]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a stirred solution of 3,4-dihydro-3-(1-methylethyl)-6-methylsulfonyl-1H-2,1,3-benzothiadiazine-2,2-dioxide (0.38 g, 0.00125 mol), triphenylphosphine (0.39 g, 0.0015 mol) and 2-(4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl)ethanol (0.26 g, 0.0015 mol) in DMF (10 ml) at −5° C. was added dropwise under nitrogen diethyl azodicarboxylate (0.24 ml, 0.0015 mol). The reaction was stirred at −5° C. for 10 mins then allowed to warm to room temperature stirring for a further 20 mins. After the addition of ethyl acetate (30 ml) and water (20 ml), the organic layer was washed with water (4×20 ml) the organics dried (MgSO4) and concentrated in vacuo to afford 0.52 g of 1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-3,4-dihydro-3-(1-methylethyl)-6-methylsulfonyl-1H-2,1,3-benzothiadiazine-2,2-dioxide as a yellow solid. Mp 118-120° C.

Workup

temperatureto warm to room temperature
stirringstirring for a further 20 mins
washthe organic layer was washed with water (4×20 ml) the
dry with materialorganics dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fcb617624b40464eb5e52c387dbb234f
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329366B1

Reaction notes

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