4-Methylmorpholine → HCID 46837081, compound

HRID 474211Notes

Reaction equation

HRID 474211 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=2)[CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]3[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=3)=[N:17]2)=[N:10][CH:11]=1.[C:32]([NH:35][C@@H:36]([CH:40]([CH3:42])[CH3:41])[C:37](O)=[O:38])(=[O:34])[CH3:33].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.ClCCl.CO.O>[C:32]([NH:35][C@@H:36]([CH:40]([CH3:42])[CH3:41])[C:37]([NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:31]=[CH:30][CH:29]=[C:14]([CH2:15][N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[N:17]3)[CH:13]=2)=[N:10][CH:11]=1)=[O:38])(=[O:34])[CH3:33]

Participants

10

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66789N-Acetyl-L-valineHCID 757711-HydroxybenzotriazoleHCID 67439967HCID 67439967, compound

Product 1

HCID 46837081HCID 46837081, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

100 mg (0.23 mmol) of 2-{3-[5-(2-aminoethoxy)pyrimidin-2-yl]benzyl}-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one hydrochloride, 43 mg (0.25 mmol) of (S)-2-acetylamino-3-methylbutyric acid, 66 mg (0.34 mmol) of EDCI, 41 mg (0.30 mmol) of HOBt are dissolved in 2 ml of DMF, and 76 μl (0.68 mmol) of 4-methylmorpholine are added. The reaction mixture is stirred at room temperature for 18 h, water is added, and the precipitate is stirred with methanol and dichloromethane. The product is dried in vacuo.

Workup

  1. customThe product is dried in vacuo

Sources & evidence

ORD record
ord-5a5a886d25454b0483bd85a4cd156513
Source dataset
uspto-grants-2014_01
Patent number
US08637518B2

Reaction notes

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