Diisopropylethylamine → HCID 59291729, compound

HRID 1809601Notes

Reaction equation

[O:1]([C:8]1[C:9]([NH:18][C:19]([NH2:21])=[S:20])=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br.[C:32]([N:35]1[CH2:40][CH2:39][CH:38]([C:41](=O)[CH2:42]Br)[CH2:37][CH2:36]1)(=[O:34])[CH3:33]>C(O)C.C(OCC)(=O)C>[O:1]([C:8]1[C:9]([NH:18][C:19]2[S:20][CH:42]=[C:41]([CH:38]3[CH2:39][CH2:40][N:35]([C:32](=[O:34])[CH3:33])[CH2:36][CH2:37]3)[N:21]=2)=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(3-phenoxy-5-(trifluoromethyl)pyridin-2-yl)thiourea (0.076 g, 0.243 mmol) was suspended in ethanol (3 mL) and diisopropylethylamine (0.127 mL, 0.728 mmol) was added, followed by 1-(1-acetylpiperidin-4-yl)-2-bromoethanone hydrobromide (0.120 g, 0.364 mmol). The mixture was heated to 60° C. and agitated for 3 hours, then diluted with ethyl acetate, washed with sodium bicarbonate, brine, dried and evaporated. The crude product was purified on silica gel (30% ethyl acetate/hexanes) to afford 1-(4-(2-(3-phenoxy-5-(trifluoromethyl)pyridin-2-ylamino)thiazol-4-yl)piperidin-1-yl)ethanone (0.065 g, 57.9% yield) as white solid. 1H NMR (d6-DMSO) δ 1.45-1.61 (m, 2H), 1.93-2.04 (m, 2H), 2.51-3.18 (m, 3H), 3.90 (d, 1H), 4.44 (d, 1H), 6.97 (s, 1H), 7.20-7.50 (m, 6H), 8.59 (s, 1H).

Workup

washwashed with sodium bicarbonate, brine
customdried
customevaporated
customThe crude product was purified on silica gel (30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-8b6efd4acfff44c998d59339f99a72c1
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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