1,2-Dichloroethane → HCID 71571668, compound

HRID 1777786Notes

Reaction equation

[O:1]=[C:2]1[N:6]2[C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1.C(Cl)CCl.[CH:30]1[CH:35]=[N:34][C:33]2N(O)N=[N:38][C:32]=2[CH:31]=1.C(N(C(C)C)CC)(C)C.NC1C=NC=CC=1>CN(C=O)C>[O:1]=[C:2]1[N:6]2[C:7]([C:11]([NH:38][C:32]3[CH:33]=[N:34][CH:35]=[CH:30][CH:31]=3)=[O:13])=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][N:3]1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In a 1-dram vial was placed 8-1 (15 mg, 0.045 mmol) in anhydrous DMF (0.45 mL). To this solution was added EDC (8.0 mg, 0.045 mmol), HOAT (6.0 mg, 0.045 mmol), diisopropylethylamine (0.008 mL, 0.045 mmol), and 3-aminopyridine (0.001 g, 0.049 mmol). The reaction mixture was heated at 40° C. and stirred for 16 h. The crude reaction mixture was then directly purified by reversed phase HPLC to give 15.0 mg (80%) of 8-2. 1H NMR (500 MHz, DMSO-d6): δ 11.06 (s, 1H), 8.84 (s, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.40 (d, J=5.0 Hz, 1H), 8.14 (d, J=8.4 Hz, 1H), 8.00 (d, J=8.0 Hz, 1H), 7.95 (d, J=8.6 Hz, 1H), 7.79 (t, J=7.4 Hz, 1H), 7.64-7.55 (m, 2H), 7.53 (t, J=6.5 Hz, 1H), 7.32 (d, J=9.3 Hz, 1H), 7.24 (t, J=7.9 Hz, 1H), 6.85 (d, J=6.5 Hz, 1H), 4.39 (t, J=7.6 Hz, 2H), 3.46 (t, J=7.6 Hz, 2H). HRMS (ES) 411.1546 (M+H) found, 411.1567 required.

Workup

customThe crude reaction mixture
customwas then directly purified by reversed phase HPLC

Sources & evidence

ORD record: ord-b1c04567135948e5925370ba85b6458b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266881B2

Reaction notes

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