2-Butanone, 3-bromo- → HCID 59300495, compound

HRID 2235925Notes

Reaction equation

[NH2:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([N:10]([CH2:30][CH2:31][CH3:32])[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C@H:20]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:19][CH2:18]3)=[N:8][CH:9]=1)=[S:3].Br[CH:34]([CH3:38])[C:35](=O)[CH3:36]>C(O)C>[CH3:38][C:34]1[N:1]=[C:2]([C:4]2[CH:5]=[CH:6][C:7]([N:10]([CH2:30][CH2:31][CH3:32])[CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[C@H:20]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:19][CH2:18]4)=[N:8][CH:9]=2)[S:3][C:35]=1[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of ethyl ((1S-5-{3-[[5-(aminocarbonothioyl)-2-pyridinyl]-(propyl)-amino]-propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 266) (90 mg, 0.20 mmol) and 3-bromo-2-butanone (40 mg, 0.26 mmol) in ethanol (9 mL) was heated under argon at 80° C. for 18 h. The solution was then concentrated and the residue purified by column chromatography (2:1 hexanes/EtOAc) to provide the title compound (0.1 g, 100%). 1H NMR (400 MHz, CD2Cl2) δ 8.54 (d, 1H), 7.89 (d, 1H), 7.06 (d, 1H), 6.79 (d, 1H), 6.71 (dd, 1H), 6.56 (d, 1H), 4.16 (q, 2H), 4.01 (t, 2H), 3.74 (t, 2H), 3.55-3.45 (m, 3H), 2.95-2.78 (m, 2H), 2.76-2.68 (m, 1H), 2.46-2.30 (m, 8H), 2.11 (qt, 2H), 1.72-1.62 (m, 3H), 1.28 (t, 3H), 0.97 (t, 3H).

Workup

concentrationThe solution was then concentrated
customthe residue purified by column chromatography (2:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-a47a36d9be7845aea4979bfd8e357b61
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714004B2

Reaction notes

Loading…