Water → HCID 23000302, compound

HRID 397569Notes

Reaction equation

[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25]([O:27][C:28](=[O:43])[CH2:29][NH:30][C:31]([C:33]1[N:37]2[N:38]=[C:39](Cl)[CH:40]=[CH:41][C:36]2=[N:35][N:34]=1)=[O:32])[CH3:26].C(N(C(C)C)C(C)C)C.O>CN(C)C=O>[CH2:25]([O:27][C:28](=[O:43])[CH2:29][NH:30][C:31]([C:33]1[N:37]2[N:38]=[C:39]([NH:18][CH2:17][CH2:16][CH2:15][N:12]3[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:10][CH2:11]3)[CH:40]=[CH:41][C:36]2=[N:35][N:34]=1)=[O:32])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

1.58 g of 4-(diphenylmethoxy)-1-piperidinepropanamine and 1.38 g of N-(6-chloro[1,2,4]triazolo[4,3-b]pyridazine-3-carbonyl)glycine ethyl ester were dissolved in 15 ml of N,N-dimethylformamide; 1.68 ml of N-ethyldiisopropylamine was added, followed by stirring under heating at an external temperature of 70° C. for 5 hours. After cooling, water was added; the reaction mixture was extracted with tetrahydrofuran. After concentration under reduced pressure, the precipitated crystal was twice recrystallized from ethanol-tetrahydrofuran (1:1), collected by filtration, and dried, to yield 995 mg of the title compound.

Workup

temperatureAfter cooling
extractionthe reaction mixture was extracted with tetrahydrofuran
concentrationAfter concentration under reduced pressure
customthe precipitated crystal was twice recrystallized from ethanol-tetrahydrofuran (1:1)
filtrationcollected by filtration
customdried

Sources & evidence

ORD record: ord-6ec256705c78465a91c596d0590b7a92
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610694B1

Reaction notes

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