2,4-Dichloro-5-fluoropyrimidine → HCID 68783568, compound

HRID 1968531Notes

Reaction equation

HRID 1968531 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[CH:4]=[N:3]1.[NH2:8][C@@H:9]1[C@@H:14]2[CH2:15][C@@H:11]([CH:12]=[CH:13]2)[C@@H:10]1[C:16]([NH2:18])=[O:17].Cl[C:20]1[N:25]=[C:24](Cl)[C:23]([C:27]([F:30])([F:29])[F:28])=[CH:22][N:21]=1.Cl[C:32]1N=C(Cl)C(F)=CN=1>>[CH2:1]([N:2]1[CH:6]=[C:5]([NH:7][C:20]2[N:25]=[C:24]([NH:8][C@@H:9]3[C@@H:14]4[CH2:15][C@@H:11]([CH2:12][CH2:13]4)[C@@H:10]3[C:16]([NH2:18])=[O:17])[C:23]([C:27]([F:30])([F:29])[F:28])=[CH:22][N:21]=2)[CH:4]=[N:3]1)[CH3:32]

Participants

5

Reactant 4

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 42580098rel-(1R,2R,3S,4S)-3-Aminobicyclo[2.2.1]hept-5-ene-2-carboxamide

Product 1

HCID 68783568HCID 68783568, compound

Procedure

The title compound was prepared as described in Example 1, substituting 1-ethyl-1H-pyrazol-4-amine for 1-methyl-1H-pyrazol-4-amine in Example 1B along with substitution of (+)-(1R,2S,3R,4S)-3-aminobicyclo[2.2.1]heptane-2-carboxamide for (+/−)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxamide and 2,4-dichloro-5-(trifluoromethyl)pyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (400 MHz, DMSO-D6) ppm 1.15 (d, J=9.77 Hz, 1H) 1.22-1.33 (m, 2H) 1.37 (t, J=7.17 Hz, 3H) 1.45-1.68 (m, 5H) 1.89 (d, J=10.07 Hz, 1H) 2.22-2.33 (m, 1H) 2.62 (d, J=8.24 Hz, 1H) 4.07 (q, J=7.22 Hz, 2H) 4.24 (t, J=7.48 Hz, 1H) 6.69-6.93 (m, 1H) 7.26-7.43 (m, 1H) 7.78 (s, 1H) 8.06 (s, 1H) 9.09 (s, 1H); MS (ESI(+)) m/e 410 (M+H)+.

Sources & evidence

ORD record
ord-78412f06c956468aac9c4b47e53b60d4
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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