Isobutyryl chloride → 6-Isopropyl-5-Oxa-7,13-Diazatetracyclo[9.3.1.02,10.04,8]Pentadeca-2(10),3,6,8-Tetraene Hydrochloride

HRID 10109

Reaction equation

HRID 10109 reaction equation
FC(F)(F)C([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[C:10]([NH2:18])[C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=O.[C:21]([Cl:26])(=O)[CH:22]([CH3:24])[CH3:23]>>[ClH:26].[CH:22]([C:24]1[O:17][C:11]2[C:10]([N:18]=1)=[CH:9][C:8]1[CH:7]3[CH2:16][CH:14]([CH2:15][NH:5][CH2:6]3)[C:13]=1[CH:12]=2)([CH3:23])[CH3:21]

Participants

3

Reactant 2

HCID 62325Isobutyryl chlorideHCID 218647172,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7), 3,5-trien-10-yl)-ethanone

Product 1

HCID 865852956-Isopropyl-5-Oxa-7,13-Diazatetracyclo[9.3.1.02,10.04,8]Pentadeca-2(10),3,6,8-Tetraene Hydrochloride

Procedure

2,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone and isobutyryl chloride were converted to the title compound following the procedures described in Example 54. (TLC 25% ethyl acetate/hexanes Rf 0.14). 1H NMR (400 MHz, CD3OD) δ 7.65 (2H), 3.49 (br s, 2H), 3.41 (d, J=12.0 Hz, 2H), 3.33–3.19 (3H), 2.45 (m, 1H), 2.18 (d, J=11.5 Hz, 1H), 1.45 (d, J=7.0 Hz, 6H). APCI MS m/e 243.2 [(M+1)+]. (HCl salt) M.p. 249–251° C.

Sources & evidence

ORD record
ord-ddf33257574b40a69f6d86c33b8b371a
Source dataset
uspto-grants-2006_08
Patent number
US07091372B2

Linked notes

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