Triethylamine → HCID 86619312, compound

HRID 2400762Notes

Reaction equation

HRID 2400762 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([NH2:22])=[CH:17][N:16]=1.C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:17]2[C:18]([NH2:22])=[CH:19][N:20]=[C:15]([Cl:14])[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2577975-Amino-2,4-dichloropyrimidine

Product 1

HCID 86619312HCID 86619312, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-t-Butoxycarbonyl-piperazine (2.36 g) was condensed with 2,4-dichloro-pyrimidin-5-ylamine (2.0 g) in dimethylsulfoxide (20 ml) in the presence of triethylamine (5.3 ml) according to the method described in Example 1, Step A. 4-(5-Amino-2-chloro-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (3.4 g) was obtained as violet crystals. MS (ES+) 314/316 (M+H+). The title product (120 mg) was obtained from this intermediate according to the methods described in Example 1, step C and D. 2-Chloro-N-(2-chloro-4-{4-[(E)-3-(4-trifluoromethoxy-phenyl)-allyl]-piperazin-1-yl}-pyrimidin-5-yl)-isonicotinamide. M.p. 210-211° C.; 1H NMR (400 MHz, CDCl3) 2.5 (m, 4H), 3.1 (d, J=9 Hz, 1H), 3.6 (m, 4H), 6.1 (dt, J=18, 9 Hz, 1H), 6.4 (d, J=18 Hz, 1H), 7.1 (d, J=11 Hz, 2H), 7.3 (d, J=11 Hz, 2H), 7.6 (d, J=5 Hz, 1H), 7.7 (s, 1H), 7.8 (s, 1H, NH), 8.4 (s, 1H), 8.5 (d, J=5 Hz, 1H); MS (ES+) 553/555 (M+H+).

Sources & evidence

ORD record
ord-15a29487cfbe4ed9a9d49817f89344c0
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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