Aluminium lithium hydride → HCID 90418235, compound

HRID 2177283Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](OCC)=[O:24])=[C:17]([CH3:28])[C:16]=2[CH3:29])=[C:11]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][CH:31]=2)[S:10][N:9]=1>>[Cl:7][C:8]1[C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[C:17]([CH3:28])[C:16]=2[CH3:29])=[C:11]([C:30]2[CH:31]=[CH:32][C:33]([CH2:36][CH3:37])=[CH:34][CH:35]=2)[S:10][N:9]=1

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418231HCID 90418231, compound

Product 1

HCID 90418235HCID 90418235, compound

Procedure

The title compound was prepared according to the procedure described in Example 156 following Step 2 by LAH reduction of ethyl 3-(4-((3-chloro-5-(4-ethylphenyl)isothiazol-4-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=7.5 Hz, 2H), 7.32 (d, J=7.5 Hz, 2H), 6.98 (d, J=6.5 Hz, 1H), 6.75 (d, J=6.5 Hz, 1H), 4.90 (s, 2H), 2.92 (t, J=7.0 Hz, 2H), 2.65 (q, J=6.8 Hz, 2H), 2.60 (t, J=7.5 Hz, 2H), 2.25 (s, 3H), 2.15 (s, 3H), 1.78 (t, J=7.6 Hz, 2H). LCMS (ESI, M/Z) for C23H26ClNO2S: 415.1, 417.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-c16d938418f645c3b71e4df258170693
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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