Hydroxyamine hydrochloride → HCID 89443543, compound

HRID 2175157Notes

Reaction equation

[ClH:1].[CH3:2][N:3]([CH3:32])[C@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([S:19][C:20]2[N:24]4[CH:25]=[C:26]([C:29](=O)[CH3:30])[CH:27]=[CH:28][C:23]4=[N:22][N:21]=2)=[CH:14][CH:13]=3)[CH2:5]1.Cl.[NH2:34][OH:35]>CO.Cl>[ClH:1].[CH3:2][N:3]([CH3:32])[C@H:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([S:19][C:20]2[N:24]4[CH:25]=[C:26](/[C:29](=[N:34]/[OH:35])/[CH3:30])[CH:27]=[CH:28][C:23]4=[N:22][N:21]=2)=[CH:14][CH:13]=3)[CH2:5]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (81.3) (12 mg, 0.026 mmol) and hydroxylamine hydrochloride (7.11 mg, 0.102 mmol) in MeOH (3 ml) was added 2 drops of HCl (2N) by a 1-ml syringe to reach pH about 3 and the mixture was stirred in a sealed tube at 85° C. for 3 h. The mixture was evaporated to dryness and the residue was purified by preparative acid HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: TFA/CH3CN 0.05%; mobile phase B: TFA/H2O 0.05%). The desired fractions were collected, evaporated by BUCHI under 30 mbar at 40° C. to remove CH3CN. The remained solution was lyophilized to afford the title compound (8.1 mg, yield 65.4%).

Workup

customThe mixture was evaporated to dryness
customthe residue was purified by preparative acid HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: TFA/CH3CN 0.05%; mobile phase B: TFA/H2O 0.05%)
customThe desired fractions were collected
customevaporated by BUCHI under 30 mbar at 40° C.
customto remove CH3CN

Sources & evidence

ORD record: ord-c56774075bf24427ba7f6c49fc3d3dc4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062045B2

Reaction notes

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