Aminoacetonitrile hydrochloride → 2-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-N-cyano methyl-acetamide

HRID 217305Notes

Reaction equation

HRID 217305 reaction equation
NC1N=C(C2C(Cl)=CC3COCC4C=3C=2C=CC=4)N=C(SCCC(O)=O)N=1.Cl.[NH2:29][CH2:30][C:31]#[N:32].[NH2:33][C:34]1[N:39]=[C:38]([C:40]2[C:41]([Cl:53])=[CH:42][C:43]3[CH2:44][O:45][CH2:46][C:47]4[C:52]=3[C:51]=2[CH:50]=[CH:49][CH:48]=4)[N:37]=[C:36]([S:54][CH2:55][C:56]([OH:58])=[O:57])[N:35]=1>>[NH2:33][C:34]1[N:39]=[C:38]([C:40]2[C:41]([Cl:53])=[CH:42][C:43]3[CH2:44][O:45][CH2:46][C:47]4[C:52]=3[C:51]=2[CH:50]=[CH:49][CH:48]=4)[N:37]=[C:36]([S:54][CH2:55][C:56]([NH:32][CH2:31][C:30]#[N:29])=[O:57])[N:35]=1.[NH2:33][C:34]1[N:39]=[C:38]([C:40]2[C:41]([Cl:53])=[CH:42][C:43]3[CH2:44][O:45][CH2:46][C:47]4[C:52]=3[C:51]=2[CH:50]=[CH:49][CH:48]=4)[N:37]=[C:36]([S:54][CH2:55][C:56]([OH:58])=[O:57])[N:35]=1

Participants

5

Reactant 3

HCID 11491918Aminoacetonitrile hydrochlorideHCID 578986383-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-propionic acidHCID 57898646[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-acetic acid

Product 2

HCID 57898646[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-acetic acidHCID 578987142-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-N-cyano methyl-acetamideYield 55%

Procedure

Proceeding in the same manner as in Step 2 of Example 205 and replacing N-methylamine hydrochloride and 3-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-propionic acid by aminoacetonitrile hydrochloride (1.91 g, 20.6 mmol) and [4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-acetic acid (2.0 g, 5.16 mmol) respectively, there was obtained 2-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-N-cyano methyl-acetamide (1.22 g, 55%) as a white solid from [4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-acetic acid (2.0 g).

Sources & evidence

ORD record
ord-57fda824bd9d447da04fa5f60f890192
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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