Ethanol → HCID 68461764, compound

HRID 2358721Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[NH2:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:40])[CH3:39])=[CH:33][CH:32]=1.[CH2:41](O)[CH3:42]>>[CH3:29][O:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:40])[CH3:39])=[CH:33][CH:32]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:41][CH3:42])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine

HCID 68459230HCID 68459230, compound

Product 1

HCID 68461764HCID 68461764, compound

Procedure

The product from Example 1d (18 mg, 0.085 mmol) was reacted in ethanol (1 mL) with the product from Example 153a (33 mg, 0.085 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (14 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.69-1.93 (m, 2 H) 2.02 (s, 3 H) 2.99 (t, J=6.99 Hz, 2 H) 3.75 (s, 3 H) 5.13 (s, 2 H) 6.29 (d, J=7.35 Hz, 1 H) 6.91 (dd, J=8.09, 2.57 Hz, 1 H) 6.95-7.05 (m, 2 H) 7.13 (d, J=8.82 Hz, 2 H) 7.16-7.24 (m, 2 H) 7.31 (t, J=8.09 Hz, 1 H) 7.38 (d, J=8.46 Hz, 1 H) 7.42 (d, J=8.82 Hz, 2 H) 7.80 (d, J=8.82 Hz, 1H) 8.35 (d, J=6.99 Hz, 1 H) 8.97 (d, J=8.82 Hz, 1 H) 9.97 (s, 1 H) 11.00 (s, 1 H) 14.36 (s,1H); MS (ESI+) m/z 565(M+H)+.

Sources & evidence

ORD record: ord-f2c32f7868f74cdca66ea26c12fad332
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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