1-Hydroxybenzotriazole → HCID 86724284, compound

HRID 594883Notes

Reaction equation

HRID 594883 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[O:9][CH2:10][C@@:11]2([N:27]=1)[C:20]1([CH2:23][O:22][CH2:21]1)[C:19]([CH3:25])([CH3:24])[O:18][C:17]1[C:12]2=[CH:13][C:14]([NH2:26])=[CH:15][CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[O:9][CH2:10][C@@:11]2([N:27]=1)[C:20]1([CH2:23][O:22][CH2:21]1)[C:19]([CH3:25])([CH3:24])[O:18][C:17]1[C:12]2=[CH:13][C:14]([NH:26][C:36]([C:33]2[CH:32]=[CH:31][C:30]([Cl:29])=[CH:35][N:34]=2)=[O:37])=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628725-Chloro-2-picolinic acidHCID 86724279HCID 86724279, compound

Product 1

HCID 86724284HCID 86724284, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl[(4S)-6′-amino-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]carbamate (1.00 g, 2.57 mmol) and CH2Cl2 (10 mL) were added 5-chloro-2-pyridinecarboxylic acid (526 mg, 3.34 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (640 mg, 3.34 mmol), 1-hydroxybenzotriazole (451 mg, 3.34 mmol) and N,N-diisopropylethylamine (0.571 mL, 3.34 mmol) at ambient temperature. After stirring overnight at the same temperature, the reaction mixture was purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 90%) and then on NH-silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 90%) to give tert-butyl[(4S)-6′-{[(5-chloropyridin-2-yl)carbonyl]amino}-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]carbamate (1.02 g).

Workup

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

Sources & evidence

ORD record
ord-635aaa96433945e6bd3f09d6b7beea4b
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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