3,4-Dichloroaniline → N-(3,4-dichlorophenyl)-5-fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]benzamide

HRID 644251Notes

Reaction equation

HRID 644251 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:19][C:18]=3[O:28][CH:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[O:14][C:13](=[O:36])[C:12]=2[CH:37]=1.[Cl:38][C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][C:45]=1[Cl:46])[NH2:42]>>[Cl:38][C:39]1[CH:40]=[C:41]([NH:42][C:13](=[O:36])[C:12]2[CH:37]=[C:8]([F:7])[CH:9]=[CH:10][C:11]=2[NH:16][C:15](=[O:14])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:19][C:18]=2[O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)[CH:43]=[CH:44][C:45]=1[Cl:46]

Participants

4

Reactant 3

HCID 72573,4-DichloroanilineHCID 23665647Potassium tert-butoxideHCID 578608426-Fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-3,1-benzoxazin-4-one

Product 1

HCID 57860836N-(3,4-dichlorophenyl)-5-fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]benzamide

Procedure

Using methods substantially equivalent to those described in Example 91-G, except using potassium t-butoxide as the base; N-(3,4-dichlorophenyl)-5-fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]benzamide was prepared from 6-fluoro-2-[2-(1-methylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-3,1-benzoxazin-4-one and 3,4-dichloroaniline.

Sources & evidence

ORD record
ord-14e25b30935041caafa5f90a8c56b42e
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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