Hydroxyamine hydrochloride → HCID 136038636, compound

HRID 2038071Notes

Reaction equation

HRID 2038071 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[NH:21][C:20]([C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]5[CH:29]=O)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[NH2:32][OH:33]>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[NH:21][C:20]([C:25]([CH3:28])([CH3:26])[CH3:27])=[C:19]5/[CH:29]=[N:32]\[OH:33])=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57700916HCID 57700916, compound

Product 1

HCID 136038636HCID 136038636, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-3-formyl-1H-indol-5-yl)cyclopropanecarboxamide (100 mg, 0.25 mmol) in dichloromethane (5 mL) was added hydroxylamine hydrochloride (21 mg, 0.30 mmol). After stirring for 48 h, the mixture was evaporated to dryness and purified by column chromatography (0-100% ethyl acetate/hexanes) to yield (Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-(2-tert-butyl-3-((hydroxyimino)methyl)-1H-indol-5-yl)cyclopropanecarboxamide (81 mg, 77%). ESI-MS m/z calc. 419.5, found 420.5(M+1)+; retention time 3.42 minutes. 1 H NMR (400 MHz, DMSO-d6) δ 10.86(s, 0.5H), 10.55(s, 0.5H), 8.56-8.50(m, 2H), 8.02(m, 1H), 7.24-7.22(m, 1H), 7.12-7.10(m, 1H), 7.03(m, 1H), 6.96-6.90 (m, 2H), 6.03(s, 2H), 1.43(s, 9H), 1.40-1.38(m, 2H), 1.04-1.01(m, 2 H).

Workup

  1. customthe mixture was evaporated to dryness
  2. custompurified by column chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f6de4c327fd148faa8a444c716be2328
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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