1-Hydroxybenzotriazole → HCID 86724251, compound

HRID 873709Notes

Reaction equation

HRID 873709 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:13]3([CH2:17][O:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:14]3)[C:10]3([CH2:12][CH2:11]3)[CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33](O)=[O:34])=[N:31][CH:32]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([NH:1][C:2]2[CH:3]=[C:4]3[C:13]4([CH2:17][O:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[N:14]4)[C:10]4([CH2:11][CH2:12]4)[CH2:9][O:8][C:5]3=[CH:6][CH:7]=2)=[O:34])=[N:31][CH:32]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628765-fluoropyridine-2-carboxylic AcidHCID 86724248HCID 86724248, compound

Product 1

HCID 86724251HCID 86724251, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (6′-aminodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl)carbamate (115 mg, 0.333 mmol), 5-fluoropyridine-2-carboxylic acid (62.3 mg, 0.433 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (83.0 mg, 0.433 mmol), 1-hydroxybenzotriazole (58.5 mg, 0.433 mmol), N,N-diisopropylethylamine (0.074 mL, 0.433 mmol) and CH2Cl2 (1.2 mL) was stirred for 2.5 days at ambient temperature. The reaction mixture was purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 10 to 90%) to afford tert-butyl (6′-{[(5-fluoropyridin-2-yl)carbonyl]amino}dispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl)carbamate (136 mg).

Workup

  1. customThe reaction mixture was purified with column chromatography on silica gel (hexane-EtOAc

Sources & evidence

ORD record
ord-bcd1ed6dacda416fa7f7529acad7cd88
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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