Pyridine → HCID 20066897, compound

HRID 1904470Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.C(Cl)Cl.Cl[C:32]([O:34][CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1)=[O:33].[C:40](OCC)(=[O:42])C>>[CH:35]1([O:34][C:32]([NH:1][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][N:8]3[CH2:11][C:12]3[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=3[O:42][CH3:40])=[CH:4][CH:3]=2)=[O:33])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Reactant 5

HCID 1049Pyridine

HCID 6344Dichloromethane

HCID 8857Ethyl Acetate

HCID 2735892Cyclopentyl chloroformate

HCID 14708763Methyl 4-(6-aminoindazol-1-ylmethyl)benzoate

Product 1

HCID 20066897HCID 20066897, compoundYield 73%

Conditions

Temperature: 25 °C

Procedure

To a mixture of indazole (L) (150 mg), pyridine (0.05 ml) and methylene chloride (2 ml), at -20° C., was added cyclopentyl chloroformate (0.07 ml). The reaction was warmed to 25° C. and stirred for 1 hour. The reaction mixture was added to ethyl acetate, and the ethyl acetate solution washed with saturated sodium carbonate, 1N HCl, and brine, and dried (MgSO4). Evaporation and trituration with diethyl ether gave methyl 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoate (M) (148 mg, 73%) as a solid; mp 150.0°-151.0° C.

Workup

washthe ethyl acetate solution washed with saturated sodium carbonate, 1N HCl, and brine
dry with materialdried (MgSO4)
customEvaporation and trituration with diethyl ether

Sources & evidence

ORD record: ord-caf4f8102313404bbd9156fdd9833fd1
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04837235

Reaction notes

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