2-Chloro-6-methylaniline → HCID 57808606, compound

HRID 2105298Notes

Reaction equation

ClC1C=CC=C(C)C=1N.ClC1C(C#N)=C(NC2C(C)=CC=CC=2Cl)N=CN=1.[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:30]=1[N:36]1[C:46]2[C:47]3[C:39](=[C:40]([C:48](O)=[O:49])[S:41][C:42]=3[N:43]=[CH:44][N:45]=2)[NH:38][C:37]1=[O:51].[N:52]1([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([NH2:65])=[CH:61][CH:60]=2)[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>>[N:52]1([CH2:58][C:59]2[CH:64]=[CH:63][C:62]([NH:65][C:48]([C:40]3[S:41][C:42]4[N:43]=[CH:44][N:45]=[C:46]5[C:47]=4[C:39]=3[NH:38][C:37](=[O:51])[N:36]5[C:30]3[C:31]([CH3:35])=[CH:32][CH:33]=[CH:34][C:29]=3[Cl:28])=[O:49])=[CH:61][CH:60]=2)[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1

Participants

Reactant 4

HCID 68972-Chloro-6-methylaniline

HCID 7768514-(Morpholinomethyl)aniline

HCID 68982327HCID 68982327, compound

HCID 86616380HCID 86616380, compound

Product 1

HCID 57808606HCID 57808606, compound

Procedure

Using the procedure of Example 1, 2-chloro-6-methyl-phenylamine Compound 48a was used in place of 3-chloro-4-fluoro-phenylamine Compound 1e to prepare 4-chloro-6-(2-chloro-6-methyl-phenylamino)-pyrimidine-5-carbonitrile Compound 48b. Using the procedure of Example 3, Compound 48b was used in place of 4-chloro-6-(2-chloro-4-fluoro-phenylamino)-pyrimidine-5-carbonitrile Compound 3b to prepare 5-(2-chloro-6-methyl-phenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,6,8-tetraaza-acenaphthylene-2-carboxylic acid Compound 4&. MS 361, 363 (MH+). Using the procedure of Example 1, Compound 48c was used in place of Compound 1 and 4-morpholin-4-ylmethyl-phenylamine Compound 3e was used in place of 4-piperidin-1-ylmethyl-phenylamine Compound 1k to prepare Compound 146. MS 535, 537 (MH+).

Sources & evidence

ORD record: ord-657db63a0ba348a888c7b3be741d22ea
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579356B2

Reaction notes

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