Hydrazine → HCID 54596661, compound

HRID 1429552Notes

Reaction equation

[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([C:26]5[CH2:31][CH2:30][N:29]([S:32]([CH2:35][CH2:36][N:37]6C(=O)C7C(=CC=CC=7)C6=O)(=[O:34])=[O:33])[CH2:28][CH:27]=5)[CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3].NN>C(Cl)Cl.CO>[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([C:26]5[CH2:31][CH2:30][N:29]([S:32]([CH2:35][CH2:36][NH2:37])(=[O:34])=[O:33])[CH2:28][CH:27]=5)[CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 2-(2-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)ethyl)isoindoline-1,3-dione (0.184 g, 0.274 mmol) in DCM (9.1 mL) and MeOH (9.1 mL) was added hydrazine (0.21 ml, 6.58 mmol). The mixture was heated in 40° C. oil bath overnight. The reaction became homogenous. The solvent was removed under reduced pressure. The residue was triturated in MeOH (6 mL) to afford desired product as a white solid (114 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 2H), 7.64 (dd, J=6.8, 5.2 Hz, 2H), 7.40 (dd, J=8.5, 1.8 Hz, 1H), 6.08 (s, 1H), 5.49-5.37 (m, 1H), 4.28-4.11 (m, 2H), 4.05 (d, J=2.8 Hz, 2H), 3.77-3.65 (m, 2H), 3.61 (t, J=5.7 Hz, 2H), 3.48-3.36 (m, 6H), 2.70 (s, 2H), 2.42 (t, J=7.5 Hz, 2H), 2.25-2.13 (m, 2H), 2.03-1.89 (m, 2H), 1.59 (dd, J=14.9, 7.4 Hz, 2H), 0.95 (t, J=7.4 Hz, 3H).

Workup

customThe solvent was removed under reduced pressure
customThe residue was triturated in MeOH (6 mL)

Sources & evidence

ORD record: ord-96ec054e8fcc4663983bd5b860963bc3
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940716B2

Reaction notes

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