2-Aminopyridine → Tert-butyl 4-(5-amino-6-(pyridin-2-ylcarbamoyl)pyrazin-2-yl)piperazine-1-carboxylate

HRID 1959358Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:21](O)=[O:22])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.N1(C(N2C=CN=C2)=O)C=CN=C1.C(N(C(C)C)C(C)C)C.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH2:51]>CN(C1C=CN=CC=1)C.CS(C)=O.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:12][CH2:13]2)=[N:4][C:3]=1[C:21](=[O:22])[NH:51][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 3-amino-6-(4-tert-butoxycarbonylpiperazin-1-yl)pyrazine-2-carboxylic acid (8.08 g, 24.99 mmol), di(imidazol-1-yl)methanone (4.863 g, 29.99 mmol), DMAP (152.7 mg, 1.250 mmol) and N-ethyl-N-isopropyl-propan-2-amine (8.074 g, 10.88 mL, 62.47 mmol) in DMSO (80.80 mL) was added pyridin-2-amine (4.704 g, 49.98 mmol) and the resulting solution stirred at 110° C. for 20 hours. Water (500 mL) was added and the mixture extracted into EtOAc (3×300 mL), dried and concentrated to give a residue which was triturated with EtOAc and filtered to give the required product as a yellow solid (5.48 g, 55% Yield).

Workup

extractionthe mixture extracted into EtOAc (3×300 mL)
customdried
concentrationconcentrated
customto give a residue which
customwas triturated with EtOAc
filtrationfiltered

Sources & evidence

ORD record: ord-ae5cb220a8ca46478e579a798604ec34
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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