Hydrochloric Acid → HCID 69422403, compound

HRID 1353945Notes

Reaction equation

HRID 1353945 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9](C1CCCCO1)[N:8]=[C:7]2[C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22](OC)=[O:23])(=[O:3])[NH2:2].[OH-].[Li+].ON1[C:36]2[N:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.[NH2:41][CH2:42][CH2:43]N1CCCCC1.Cl.C(N=C=NCCCN(C)C)C.Cl>O1CCCC1.O.O1CCOCC1>[NH:37]1[CH2:38][CH2:39][CH2:40][CH2:35][CH:36]1[CH2:43][CH2:42][NH:41][C:22]([C:21]1[CH:20]=[C:19]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([C:1]([NH2:2])=[O:3])[CH:5]=3)[NH:9][N:8]=2)[CH:28]=[CH:27][CH:26]=1)=[O:23]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 33944N-(2-Aminoethyl)piperidineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22479679HCID 22479679, compound

Product 1

HCID 69422403HCID 69422403, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared as described in Example 381 E, using methyl 3-(5-carbamoyl-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)benzoate (0.297 g, 0.78 mmol) and lithium hydroxide (0.102 g, 2.43 mmol) in tetrahydrofuran (2.5 mL) and water (2 mL); 1-hydroxy-7-azabenzotriazole (0.325 g, 2.39 mmol), 1-(2-aminoethyl)piperidine (0.335 mL, 2.39 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.452 g, 2.35 mmol), and additional tetrahydrofuran (2 mL); 4 N hydrochloride solution in dioxane (10 mL). The final cride product was purified by preparative HPLC (5–40% acetonitrile to H2O, 30 min.) (0.025 g, 8% yield over 3 steps): 1H NMR (CD3OD) δ 8.71 (s, 1H), 8.47 (t, 1H), 8.19 (dt, 1H), 8.01 (dd, 1H), 7.91 (dt, 1H), 7.66 (t, 2H), 3.62 (t, 2H), 2.65 (t, 2H), 2.57 (br s, 4H), 1.65 (m, 4H), 1.51 (d, 2H); ES-MS (m/z) 392.4 [M+1]+.

Workup

  1. customThe final cride product was purified by preparative HPLC (5–40% acetonitrile to H2O, 30 min.) (0.025 g, 8% yield over 3 steps)

Sources & evidence

ORD record
ord-51a89459433346db9d6e56ab3664011b
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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