Hydroxyamine hydrochloride → HCID 136343918, compound

HRID 1012940Notes

Reaction equation

HRID 1012940 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([C@H:14]3[O:19][CH2:18][C@H:17]([NH:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]5[S:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=5[N:31]=4)[CH2:16][CH2:15]3)=O)[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[NH2:34][OH:35]>N1C=CC=CC=1>[OH:35][N:34]=[C:12]([C:10]1[S:11][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)[C@H:14]1[O:19][CH2:18][C@H:17]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[S:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=3[N:31]=2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11998933HCID 11998933, compound

Product 1

HCID 136343918HCID 136343918, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3R,6S)-6-{[6-(4-methoxy-benzothiazole-2-carbonyl)-tetrahydro-pyran-3-ylamino]-methyl}-4H-pyrido[3,2-b][1,4]thiazin-3-one (Example 29, 47 mg, 0.1 mmol), and hydroxylamine hydrochloride (5 eq) in pyridine (1 ml) was stirred at RT overnight. The mixture was concentrated in vacuo and partitioned between NH4OH and DCM. The organic layers were dried over MgSO4 and concentrated. Chromatography on SiO2 (EtOAc/MeOH 9:1 +1% NH4OH) gave the title compound as yellow solid (10 mg, 20%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between NH4OH and DCM
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14a4a5ba7e4f4df58c93aa68e586d69a
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

Loading…