Hydrochloric Acid → HCID 68891892, compound

HRID 1821010Notes

Reaction equation

[OH-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[S:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:22][C:21]=3[CH3:33])[N:16]=2)[CH:8]=[CH:9][C:10]=1[S:11][CH:12]([CH3:14])[CH3:13])#[N:4].Cl>C(O)C>[C:3]([C:5]1[CH:6]=[C:7]([C:15]2[S:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][C:21]=3[CH3:33])[N:16]=2)[CH:8]=[CH:9][C:10]=1[S:11][CH:12]([CH3:14])[CH3:13])#[N:4]

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium hydroxide (5 N) (0.44 mmol, 0.1 mL) was added to a solution of ethyl 3-(4-(5-(3-cyano-4-isopropylthiophenyl)-1,3,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (0.09 mmol, from Step D) in ethanol (2 mL). The reaction mixture was stirred at 50° C. for 1 h. The reaction was acidified to a pH<7 with 2 N HCl and the product was extracted with EtOAc (20 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 10% methanol/methylene chloride yielded 12 mg of the title compound: 1H NMR (500 MHZ, CDCl3) δ 8.26 (s, 1H), 8.24 (d, J=8.3, H), 7.74 (d, J=7.7, 1H), 7.62 (d, J=8.3, 1H), 7.28 (s, 1H), 7.24 (d, J=8.0, 1H), 3.70-3.78 (m, 1H), 3.02-3.10 (m, 2H), 2.76-2.82 (m, 2H), 2.68 (s, 3H), 1.47 (d, J=6.4, 6H); ESI-MS (m/z) 423.9; HPLC A: 3.79 min.

Workup

extractionthe product was extracted with EtOAc (20 mL)
dry with materialThe organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
washSilica gel chromatography eluting with 10% methanol/methylene chloride

Sources & evidence

ORD record: ord-b0d02fea4e344587ba5cf64c2e9973f6
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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