8-Chloro-3-methoxy-1,5-naphthyridine → HCID 59843019, compound

HRID 1878710Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.[NH2:14][CH2:15][CH2:16][N:17]1[CH:22]=[C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:19][C:18]1=[O:28]>CC(O)C>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:14][CH2:15][CH2:16][N:17]3[CH:22]=[C:21]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[CH:20]=[CH:19][C:18]3=[O:28])=[CH:3][CH:4]=[N:5]2)=[N:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 8-chloro-3-methoxy-1,5-naphthyridine (35 mg, 182 μmol) and 1-(2-aminoethyl)-5-(thiophen-2-yl)pyridin-2(1H)-one (40 mg, 182 μmol) in iPrOH (0.5 mL) was heated to 100° C. overnight. The mixture was partitioned between CH2Cl2 (10 mL) and 1M NaOH (5 mL). The aqueous was further extracted with CH2Cl2 (2×5 mL) and combined organics dried over MgSO4 then purified on silica (12 g) eluting with 15-60% of 5% (MeOH/CH2Cl2). MS (ESI pos. ion) m/z (MH+): 379. Calc'd exact mass for C20H18N4O2S: 378. 1H NMR (400 MHz, Chloroform-d) 8 ppm 3.09 (br. s., 1H) 3.85 (q, J=6.13 Hz, 2H) 3.93 (s, 3H) 4.28 (t, J=5.97 Hz, 2H) 6.57 (d, J=5.48 Hz, 1H) 6.65 (d, J=9.59 Hz, 1H) 6.81 (d, J=2.74 Hz, 1H) 6.91-7.00 (m, 2H) 7.10-7.15 (m, 1H) 7.34 (d, J=2.54 Hz, 1H) 7.50-7.58 (m, 2H) 8.40 (d, J=2.74 Hz, 1H) 8.45 (d, J=5.48 Hz, 1H).

Workup

customThe mixture was partitioned between CH2Cl2 (10 mL) and 1M NaOH (5 mL)
extractionThe aqueous was further extracted with CH2Cl2 (2×5 mL)
dry with materialcombined organics dried over MgSO4
customthen purified on silica (12 g)
washeluting with 15-60% of 5% (MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-48c646f26ac64bc18bcfe0024a88af4b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314087B2

Reaction notes

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