Aluminium lithium hydride → HCID 90418130, compound

HRID 2177287Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:12]([CH2:13][O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][C:24](OCC)=[O:25])=[CH:17][C:16]=2[F: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[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][C:16]=2[F: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 90417976HCID 90417976, compound

Product 1

HCID 90418130HCID 90418130, 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)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 7.51 (d, J=8.0 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 6.80 (d, J=9.2 Hz, 2H), 5.08 (s, 2H), 3.58 (t, J=6.4 Hz, 2H), 2.63-2.75 (m, 4H), 1.80-1.84 (m, 2H), 1.30 (t, J=7.6 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H20ClF2NO2S, 424.1 (M+H). found 424.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-717faa1467174f82ba5524ba84c61139
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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