Diisopropylethylamine → 6-(3,5-Bis-tert-butoxycarbonylamino-piperidin-1-yl)-3-chloro-pyridazine-4-carboxylic acid

HRID 1354831Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[C:12]([O:16][C:17]([NH:19][C@@H:20]1[CH2:25][C@H:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][NH:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>CN(C=O)C>[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:25][CH:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][N:22]([C:5]2[N:4]=[N:3][C:2]([Cl:1])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=2)[CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3,6-Dichloro-pyridazine-4-carboxylic acid (201) (400 mg, 2 mmol) and (3R,5S)-3,5-bis-tert butoxy carbonyl amino piperdine (4) (1.3 g, 4 mmol) in 14 ml DMF containing iPr2NEt (718 ∥l, 4 mmol) was heated at 100° C. for 25.6 h with shaking. The solvent was removed under reduced pressure. After HPLC purification, compound 207 (483 mg, 51.1%) was obtained as a solid. LC-MS (ESI): m/e=472.3 [M+1]+

Workup

customThe solvent was removed under reduced pressure
customAfter HPLC purification

Sources & evidence

ORD record: ord-fda00138062b4a6db712dd8754128ca8
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223759B2

Reaction notes

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