2,4,5-Trichloropyrimidine → HCID 68783820, compound

HRID 1968537Notes

Reaction equation

HRID 1968537 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]([Cl:27])=[CH:22][N:21]=1.ClC1N=[C:33](Cl)[C:32](F)=[CH:31]N=1>>[Cl:27][C:23]1[C:22]([NH:8][C@@H:9]2[C@@H:14]3[CH2:15][C@@H:11]([CH:12]=[CH:13]3)[C@@H:10]2[C:16]([NH2:18])=[O:17])=[N:21][C:20]([NH:7][C:5]2[CH:4]=[N:3][N:2]([CH:1]3[CH2:33][CH2:32][CH2:31]3)[CH:6]=2)=[N:25][CH:24]=1

Participants

5

Reactant 4

HCID 2372592,4,5-TrichloropyrimidineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 42580098rel-(1R,2R,3S,4S)-3-Aminobicyclo[2.2.1]hept-5-ene-2-carboxamide

Product 1

HCID 68783820HCID 68783820, compound

Procedure

The title compound was prepared as described in Example 1, substituting 1-cyclobutyl-1H-pyrazol-4-yl-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 2,4,5-trichloropyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.42 (d, J=8.82 Hz, 1H) 1.71-1.83 (m, 2H) 2.11 (d, J=8.82 Hz, 1H) 2.29-2.46 (m, 4H) 2.77 (s, 1H) 2.88 (s, 1H) 4.14 (t, J=7.97 Hz, 1H) 4.65-4.81 (m, 1H) 6.28 (d, J=8.48 Hz, 1H) 6.38 (d, J=8.14 Hz, 1H) 7.24 (s, 1H) 7.53 (s, 1H) 7.68 (s, 1H) 7.79 (s, 2H) 7.89 (s, 1H) 9.09 (s, 1H); MS (ESI(+)) m/e 400 (M+H)+.

Sources & evidence

ORD record
ord-5c411fae365b423ea9b1034be9f4e502
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

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