6-Amino-3-chloropyridazine → HCID 58869810, compound

HRID 2402306Notes

Reaction equation

HRID 2402306 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13](NC1C=CC(C(O)=O)=CN=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:7]2=[O:33].[NH2:34][C:35]1[N:36]=[N:37][C:38]([Cl:41])=[CH:39][CH:40]=1>>[Cl:41][C:38]1[N:37]=[N:36][C:35]([NH:34][C:13](=[O:14])[CH2:12][CH2:11][CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:7](=[O:33])[N:8]2[CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid

Product 1

HCID 58869810HCID 58869810, compound

Procedure

The product of Example 11, Part D (150 mg, 0.453 mmol) and 3-amino-6-chloropyridazine (57.3 mg, 0.453 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (112 mg, 18%). 1H NMR (400 MHz, CDCl3) δ 9.71 (s, 1H), 8.45 (d, J=9 Hz, 1H), 7.61 (d, J=8 Hz, 1H); 7.49 (d, J=9 Hz, 1H); 7.39 (m, 1H); 7.30 (m, 2H), 7.17 (t, J=9 Hz, 1H); 7.01 (t, J=8.5 Hz, 2H); 5.29 (d, J=15 Hz, 1H), 4.69 (m, 1H), 4.25 (d, J=15 Hz, 1H), 2.63-2.52 (m, 2H); 2.29-2.17 (m, 2H). MS: m/z (MH+) 443.

Sources & evidence

ORD record
ord-e65e8b9c555f4201a9eec6a29c5ff9ed
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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