Sodium Carbonate → HCID 11303601, compound

HRID 2242918Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([NH2:16])[C:5]2[N:6]([N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:7]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]=[C:27]([C:2]2[N:3]=[C:4]([NH2:16])[C:5]3[N:6]([N:8]=[C:9]([C:11]4[O:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)[CH:7]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (112 mg, 0.4 mmol; see Examples 1 and 2), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (185 mg, 0.6 mmol; see Eastwood, P. Tetrahedron Letters 41:3705-3708 (2000) for its preparation), Pd(PPh3)3 (28 mg, 0.024 mmol), and aqueous Na2CO3 (2 M, 1 mL) in DMF (4 mL) was heated (at approximately 80° C.) for 16 hours. The reaction was filtered and then purified by HPLC (C18, H2O:MeCN gradient) to afford 4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (72 mg, 47%). 1H NMR (400 MHz, DMSO-d6) δ 1.43 (s, 9H), 2.47 (br. s, 2H), 3.54 (t, j=6.2 Hz, 2H), 4.05 (br. s, 2H), 6.7 (br. s, 1H), 6.7 (dd, J=3.3, 1.7 Hz, 1H), 7.12 (dd, J=3.5, 0.7 Hz, 1H), 7.91 (dd, J=1.7, 0.7 Hz, 1H), 8.18 (s, 1H). MS. m/z 383 [M+H]+

Workup

filtrationThe reaction was filtered
custompurified by HPLC (C18, H2O:MeCN gradient)

Sources & evidence

ORD record: ord-f096436bf1dc41d3b0d7ea61d42e18fb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674791B2

Reaction notes

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