Iodide Ion → 3-(4,4-difluorocyclohexyl)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide

HRID 15000

Reaction equation

HRID 15000 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[CH:20]=[CH:19][C:18]2[S:17](=[O:22])(=[O:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10](C(OC(C)(C)C)=O)[C:9]=2[CH:8]=1)=O)C.[F:30][C:31]1([F:39])[CH2:36][CH2:35][CH:34]([CH2:37]I)[CH2:33][CH2:32]1.FC1(F)CCC(C(OCC)=O)CC1.[I-].[CH3:54][N:55]1[CH:59]=[CH:58][C:57]([NH2:60])=[N:56]1>>[F:30][C:31]1([F:39])[CH2:36][CH2:35][CH:34]([CH2:37][CH:6]([C:7]2[CH:20]=[CH:19][C:18]3[S:17](=[O:22])(=[O:21])[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]=3[CH:8]=2)[C:4]([NH:60][C:57]2[CH:58]=[CH:59][N:55]([CH3:54])[N:56]=2)=[O:3])[CH2:33][CH2:32]1

Participants

6

Reactant 5

HCID 30165Iodide IonHCID 1372541-Methyl-3-aminopyrazoleHCID 2779138Ethyl-4,4-difluorocyclohexane carboxylateHCID 59340981tert-butyl 2-ethoxycarbonylmethyl-5,5-dioxo-5H-phenothiazine-10-carboxylateHCID 672369851,1-Difluoro-4-(iodomethyl)cyclohexane

Product 1

HCID 580242303-(4,4-difluorocyclohexyl)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide

Procedure

Analogously to Example 36 and Example 44, tert-butyl 2-ethoxycarbonylmethyl-5,5-dioxo-5H-phenothiazine-10-carboxylate, 1,1-difluoro-4-iodomethylcyclohexane (prepared from commercially available ethyl 4,4-difluorocyclohexanecarboxylate analogously to the synthesis of the iodide described in Example 40) and 1-methyl-1H-pyrazol-3-amine give 3-(4,4-difluorocyclohexyl)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-N-(1-methyl-1H-pyrazol-3-yl)propionamide.

Sources & evidence

ORD record
ord-9bb50b18badf4dd7903ca55bbb1fedd2
Source dataset
uspto-grants-2010_06
Patent number
US07732440B2

Linked notes

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