Hydrochloric Acid → HCID 178521846, compound

HRID 1349893Notes

Reaction equation

HRID 1349893 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:41]=[C:42]([CH:47]=[CH:48][CH:49]=2)[C:43](OC)=[O:44])=[N:8]1.[OH-].[Li+].ON1C2C=CC=CC=2N=N1.[CH:62]1([NH2:67])[CH2:66][CH2:65][CH2:64][CH2:63]1.Cl.C(N=C=NCCCN(C)C)C.Cl>O1CCCC1.O.O1CCOCC1>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:41]=[C:42]([C:43]([NH:67][CH:62]3[CH2:66][CH2:65][CH2:64][CH2:63]3)=[O:44])[CH:47]=[CH:48][CH:49]=2)=[N:17]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 2906CyclopentylamineHCID 3939Lithium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22479977HCID 22479977, compound

Product 1

HCID 178521846HCID 178521846, compoundYield 5%

Reagents, catalysts & solvents 3

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

Procedure

The title compound was prepared as described in Example 381, using methyl 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}benzoate (0.402 g, 0.62 mmol) and lithium hydroxide (0.045 g, 1.88 mmol) in tetrahydrofuran (3 mL) and water (2 mL); 1-hydroxybenzotriazole (0.253 g, 1.87 mmol), cyclopentylamine (0.184 mL, 1.87 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.360 g, 1.88 mmol), and additional tetrahydrofuran (2 mL); 4 N hydrochloride solution in dioxane (10 mL). The final crude product was purified by preparative HPLC (10–90% acetonitrile to H2O, 20 min.) (0.012 g, 5% yield over 3 steps): 1H NMR (CD3OD) δ 8.80 (s, 1H), 8.44 (s, 1H), 8.20 (d, 1H), 8.13 (d, 1H), 7.89 (dd, 1H), 7.70 (d, 1H), 7.66 (t, 1H), 3.60 (m, 1H), 2.07 (m, 2H), 1.82 (m, 2H), 1.68 (m, 4H); ES-MS (m/z) 373 [M+1]+.

Workup

  1. customThe final crude product was purified by preparative HPLC (10–90% acetonitrile to H2O, 20 min.) (0.012 g, 5% yield over 3 steps)

Sources & evidence

ORD record
ord-af139af66d54497c92916821f309965a
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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