2,4-Dichloro-5-fluoropyrimidine → HCID 68780940, compound

HRID 1968527Notes

Reaction equation

HRID 1968527 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]([CH:12]=[CH: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 68780940HCID 68780940, 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 (+)-(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-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 (300 MHz, DMSO-D6) ppm 1.28-1.47 (m, 4H) 2.03 (d, J=8.82 Hz, 1H) 2.86 (d, J=13.2 Hz, 2H) 4.08 (q, J=7.1 Hz, 2H) 4.17 (t, J=6.8 Hz, 1H) 6.28 (dd, J=5.6, 2.88 Hz, 1H) 6.38 (s, 1H) 7.30 (s, 1H) 7.59 (s, 1H) 7.77 (d, J=22.4 Hz, 3H) 8.11 (s, 2H) 9.20-9.66 (m, 1H); MS (ESI(+)) m/e 408 (M+1)+.

Sources & evidence

ORD record
ord-b6ebd157d6044d6ea475451dfd4f3084
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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