Triethylamine → HCID 59293922, compound

HRID 1930779Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:20]([NH2:25])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1.[C:28]([O:32][C:33](=[O:48])[C@@H:34]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:36][C:37](O)=[O:38])([CH3:31])([CH3:30])[CH3:29].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.O>[C:28]([O:32][C:33](=[O:48])[C@@H:34]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:36][C:37](=[O:38])[NH:25][C:20]1[C:19]([C:17]2[O:16][N:15]=[C:14]([CH2:13][C:12]3[CH:26]=[CH:27][C:9]([CH2:8][O:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[CH:10][CH:11]=3)[CH:18]=2)=[CH:24][CH:23]=[CH:22][N:21]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(3-(4-(pyridin-2-yloxymethyl)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (900 mg, 2.5 mmol) described in Reference Example 1 in acetonitrile (15 mL) were added (S)-2-tert-butoxycarbonylamino-pentanedioic acid 1-tert-butyl ester (860 mg, 2.8 mmol), triethylamine (0.37 mL, 2.6 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (1.1 g, 2.8 mmol) at 0° C., which was stirred overnight at 60° C. Water and ethyl acetate were added to the reaction solution, and the organic layer was washed with saturated brine. The residue thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1), so as to obtain the titled compound (980 mg).

Workup

washthe organic layer was washed with saturated brine
customThe residue thus obtained
customwas purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-5122496f1d414711a415778376309b51
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188119B2

Reaction notes

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