Dichloromethane → 5-(8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino)-1,3-dihydro-indol-2-one

HRID 2272995Notes

Reaction equation

HRID 2272995 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)=[C:2]=S.C1(C([O-])=O)C=C(C)C=C(C)C=1.[NH2:25][N+:26]1[CH:31]=[CH:30][N:29]=[CH:28][C:27]=1[NH2:32].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.[Cl:53]CCl>>[Cl:53][C:28]1[C:27]2[N:26]([N:25]=[C:2]([NH:1][C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[NH:9][C:8](=[O:13])[CH2:7]4)[N:32]=2)[CH:31]=[CH:30][N:29]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 824909265-Isothiocyanato-1,3-dihydro-indol-2-oneHCID 1317328011,2-Diamino-pyrazinium mesitylenate

Product 1

HCID 866943415-(8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino)-1,3-dihydro-indol-2-oneYield 55%

Procedure

To a solution of 5-isothiocyanato-1,3-dihydro-indol-2-one (2.3 g, 12.09 mmol) in dry dichloromethane (200 ml), 1,2-diamino-pyrazinium mesitylenate (5.21 g, 15.12 mmol), diisopropylethylamine (7.81 g, 60.45 mmol) and EDCI (4.63 g, 24.18 mmol) are added and stirred for 6 hours. The reaction mixture is concentrated and the residue is taken in water (100 ml), triturated and filtered, the crude solid is purified by silica column using (60-120) mesh to get the titled product as yellow solid (2.0 g, 55%);

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customtriturated
  3. filtrationfiltered
  4. customthe crude solid is purified by silica column

Sources & evidence

ORD record
ord-e34be8bf2daa44d6940847897925da90
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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