O-Methylhydroxylamine hydrochloride → HCID 87222433, compound

HRID 712275Notes

Reaction equation

HRID 712275 reaction equation
Cl.[CH3:2][O:3][NH2:4].[C:5]([C:8]1[C:16]2[S:15][C:14]([NH:17][C:18](=[O:22])[NH:19][CH2:20][CH3:21])=[N:13][C:12]=2[CH:11]=[C:10]([C:23]2[CH:24]=[N:25][C:26]([N:29]3[CH2:34][CH2:33][C:32]([CH3:40])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30]3)=[N:27][CH:28]=2)[CH:9]=1)(=O)[CH3:6]>CN(C=O)C>[CH2:20]([NH:19][C:18]([NH:17][C:14]1[S:15][C:16]2[C:8](/[C:5](/[CH3:6])=[N:4]/[O:3][CH3:2])=[CH:9][C:10]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:30][CH2:31][C:32]([CH3:40])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:34]4)=[N:25][CH:24]=3)=[CH:11][C:12]=2[N:13]=1)=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 86663987Ethyl 1-[5-[7-acetyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 87222433HCID 87222433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

O-Methyl hydroxylamine hydrochloride (64 mg, 0.784 mmol) was added to ethyl 1-[5-[7-acetyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (200 mg, 0.39 mmol) in DMF (5 mL). The reaction mixture was heated to 60° C. for 4 h after which time LCMS indicated clean conversion to the desired product. The reaction was diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo. The crude product obtained was used in the next step.

Sources & evidence

ORD record
ord-11fe1b5aad664f1382a5c5a780db6bbe
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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