1-Hydroxybenzotriazole → Tert-butyl (6'-{[(5-chloropyridin-2-yl)carbonyl]amino}-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)carbamate

HRID 594856Notes

Reaction equation

HRID 594856 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:24](=[CH:25][CH:26]=1)[O:23][C:22]([CH3:28])([CH3:27])[C:18]1([CH2:21][O:20][CH2:19]1)[C:5]12[CH2:9][O:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:6]1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36](O)=[O:37])=[N:34][CH:35]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH:1][C:2]2[CH:3]=[C:4]3[C:24](=[CH:25][CH:26]=2)[O:23][C:22]([CH3:28])([CH3:27])[C:18]2([CH2:21][O:20][CH2:19]2)[C:5]23[CH2:9][O:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[N:6]2)=[O:37])=[N:34][CH:35]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628725-Chloro-2-picolinic acidHCID 86724249Tert-butyl (6'-amino-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)carbamate

Product 1

HCID 86724252Tert-butyl (6'-{[(5-chloropyridin-2-yl)carbonyl]amino}-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (6′-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)carbamate (878 mg, 2.25 mmol), 5-chloro-2-pyridinecarboxylic acid (476 mg, 2.93 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (562 mg, 2.93 mmol), 1-hydroxybenzotriazole (396 mg, 2.93 mmol), N,N-diisopropylethylamine (0.502 mL, 2.93 mmol) and CH2Cl2 (8.78 mL) was stirred for 1.5 hours at ambient temperature. After concentration of the reaction mixture at reduced pressure, the residue was purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 90%) to give tert-butyl (6′-{[(5-chloropyridin-2-yl)carbonyl]amino}-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)carbamate (976 mg).

Workup

  1. customAfter concentration of the reaction mixture at reduced pressure, the residue was purified with column chromatography on silica gel (hexane-EtOAc

Sources & evidence

ORD record
ord-721810cd46d940cba2aee1904d5cafa0
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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