Hydroxyamine hydrochloride → HCID 11308008, compound

HRID 1830999Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:47]=[CH:48][C:49]=1[O:50][CH3:51])[CH2:6][NH:7][C:8](=[O:46])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17](=[O:45])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][CH:26]([NH:28][CH2:29][C@@H:30]([C:32]3[CH:33]=[N:34][C:35]([N:38]4C(C)=CC=C4C)=[CH:36][CH:37]=3)[OH:31])[CH3:27])[CH:20]=2)=[CH:11][CH:10]=1.Cl.NO>C(O)C>[NH3:7].[NH2:38][C:35]1[N:34]=[CH:33][C:32]([C@@H:30]([OH:31])[CH2:29][NH:28][CH:26]([CH3:27])[CH2:25][C:21]2[CH:20]=[C:19]([CH2:18][C:17]([NH:16][CH2:15][C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]4[CH:47]=[CH:48][C:49]([O:50][CH3:51])=[C:3]([O:2][CH3:1])[CH:4]=4)=[O:46])=[CH:10][CH:11]=3)=[O:45])[CH:24]=[CH:23][CH:22]=2)=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of N-(3,4-dimethoxy-benzyl)-4-({2-[3-(2-{(2R)-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-2-hydroxy-ethylamino}-propyl)-phenyl]-acetylamino}-methyl)-benzamide (48 mg, 0.07 mmol) in ethanol (1 ml) was treated with hydroxylamine hydrochloride (24 mg, 0.35 mmol) and the resulting mixture heated in a Reactivial™ at 80° C. for 16 hours. The reaction mixture was cooled, passed through a Strong Cation Exchange column eluting with methanol and then 2N ammonia in methanol to elute the product. Further purification by flash column chromatography eluting with dichloromethane:methanol:880 ammonia (97:3:0.5 changing to 90:10:1 by volume) gave the title compound (28 mg) as a pale yellow foam.

Workup

temperatureThe reaction mixture was cooled
washeluting with methanol
wash2N ammonia in methanol to elute the product
customFurther purification by flash column chromatography
washeluting with dichloromethane

Sources & evidence

ORD record: ord-52c17fe5f3dc4f4685c3d41bd5f10f3d
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067541B2

Reaction notes

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