Triphenylphosphine → HCID 57812738, compound

HRID 912072Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[C:23]4[CH:24]=[N:25][C:26]([N+:29]([O-])=O)=[C:27](O)[C:22]=4[O:21][CH:20]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[N:37]([C:39]([C@H:42]([OH:44])[CH3:43])=[N:40][N:41]=2)[N:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>Cl.[Fe].CCO.C1COCC1>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]2[N:37]([C:39]([C@@H:42]([O:44][C:27]3[C:22]4[O:21][CH:20]=[C:19]([C:17]5[CH:16]=[N:15][N:14]([CH:11]6[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]6)[CH:18]=5)[C:23]=4[CH:24]=[N:25][C:26]=3[NH2:29])[CH3:43])=[N:40][N:41]=2)[N:38]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of 4-[4-(7-hydroxy-6-nitrofuro[3,2-c]pyridin-3-yl)pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester (50.0 mg, 0.116 mmol), (R)-1-(6-chloro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethanol (46.2 mg, 0.233 mmol), triphenylphosphine (122 mg, 0.466 mmol) and THF (5 mL) under nitrogen at rt was added diisopropyl azodicarboxylate (0.09 mL, 0.466 mmol) dropwise. The solution was heated to 40° C. overnight. The solvent was removed in vacuo, and EtOH (8 mL), iron powder (60 mg, 1 mmol) and conc. HCl (8 drops) were added. The mixture was heated to 75° C. for 2 h. The material was loaded into a SCX cartridge, washed with MeOH and ejected with 2M NH3 in MeOH. The filtrate was concentrated in vacuo to afford the title compound as a dark orange solid, and was used in the next step without further purification.

Workup

additionwere added
temperatureThe mixture was heated to 75° C. for 2 h
washwashed with MeOH
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-c03e63d44f114a59849adb559661d2ae
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022206B2

Reaction notes

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