Aluminium lithium hydride → HCID 90417915, compound

HRID 2177249Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:9]=[C:10]([CH2:34][CH2:35][C:36](OCC)=[O:37])[CH:11]=[C:12]([F:33])[C:13]=1[O:14][CH2:15][C:16]1[C:17]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[N:18][S:19][C:20]=1[C:21]([F:24])([F:23])[F:22]>>[F:7][C:8]1[CH:9]=[C:10]([CH2:34][CH2:35][CH2:36][OH:37])[CH:11]=[C:12]([F:33])[C:13]=1[O:14][CH2:15][C:16]1[C:17]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[N:18][S:19][C:20]=1[C:21]([F:24])([F:22])[F:23]

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418756HCID 90418756, compound

Product 1

HCID 90417915HCID 90417915, compound

Procedure

The title compound was prepared according to the procedure described in Example 110 by LAH reduction of ethyl 3-(3,5-difluoro-4-((3-(6-methoxypyridin-3-yl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)phenyl)propanoate to afford the desired product as an off-white solid. 1HNMR (300 MHz, CD3OD) δ 8.57 (s, 1H), 8.13 (d, J=8.7 Hz, 1H), 6.84-6.93 (m, 3H), 5.23 (s, 2H), 3.99 (s, 3H), 3.56 (t, J=6.3 Hz, 2H), 2.65 (t, J=8.1 Hz, 2H), 1.80-1.85 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C20H17F5N2O3S, 461.1 (M+H). found 461.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-6ce6e04d056a429caf42de8d463a88dd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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