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

HRID 14999

Reaction equation

HRID 14999 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-].[CH2:54]([N:61]1[CH:65]=[CH:64][C:63]([NH2:66])=[N:62]1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>>[CH2:54]([N:61]1[CH:65]=[CH:64][C:63]([NH:66][C:4](=[O:3])[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)[CH2:37][CH:34]2[CH2:35][CH2:36][C:31]([F:39])([F:30])[CH2:32][CH2:33]2)=[N:62]1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

6

Reactant 5

HCID 30165Iodide IonHCID 15086161-benzyl-1H-pyrazol-3-amineHCID 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 58024228N-(1-benzyl-1H-pyrazol-3-yl)-3-(4,4-difluorocyclohexyl)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-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-difluoro-cyclohexanecarboxylate analogously to the synthesis of the iodide described in Example 40) and 1-benzyl-1H-pyrazole-3-ylamine give N-(1-benzyl-1H-pyrazol-3-yl)-3-(4,4-difluorocyclohexyl)-2-(5,5-dioxo-5,10-dihydrophenothiazin-2-yl)propionamide.

Sources & evidence

ORD record
ord-47e6c27b4fcb4545a373f8401d430330
Source dataset
uspto-grants-2010_06
Patent number
US07732440B2

Linked notes

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