HCID 86618700, compound → HCID 68713332, compound

HRID 2239380Notes

Reaction equation

HRID 2239380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:38][C:11]3[C:12](=[O:37])[N:13]([CH2:16][C:17]4[N:22]=[C:21]([O:23][CH2:24][C@H:25]5[CH2:29][CH2:28][CH2:27][N:26]5C(OC(C)(C)C)=O)[CH:20]=[CH:19][CH:18]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:38][C:11]3[C:12](=[O:37])[N:13]([CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([O:23][CH2:24][C@H:25]5[CH2:29][CH2:28][CH2:27][NH:26]5)[N:22]=4)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86618700HCID 86618700, compound

Product 1

HCID 68713332HCID 68713332, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (2R)-2-{[(6-{[2-(4-chlorophenyl)-7-oxothieno[2,3-d]pyridazin-6(7H)-yl]methyl}pyridin-2-yl)oxy]methyl}pyrrolidine-1-carboxylate (380 mg, 0.69 mmol) was dissolved in 4M HCl in dioxane (1 mL) and stirred at ambient temperature for 3 h. The solvent was evaporated and the title compound was used directly in the next step. Yield: 310 mg (99%). 1H NMR (399.961 MHz, CDCl3) δ 8.39 (s, 1H), 7.89 (t, J=8.0 Hz, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.50 (s, 1H), 7.41 (d, J=8.7 Hz, 2H), 7.15 (d, J=7.5 Hz, 1H), 7.07 (d, J=8.5 Hz, 1H), 5.59 (d, J=14.9 Hz, 1H), 5.42 (d, J=14.9 Hz, 1H), 4.83-4.71 (m, 1H), 4.58-4.51 (m, 1H), 4.17-4.06 (m, 1H), 3.47-3.28 (m, 2H), 2.27-2.02 (m, 3H), 1.98-1.84 (m, 1H). MS (ESI+) 453.2 (M+1H+)

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-20f416019c664a38963054739c39bb81
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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