2,4-Dichloro-5-fluoropyrimidine → HCID 68781666, compound

HRID 1968543Notes

Reaction equation

HRID 1968543 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]([Br:27])=[CH:22][N:21]=1.ClC1N=[C:33](Cl)[C:32](F)=[CH:31]N=1>>[Br: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]([CH2:1][CH2:33][C:32]3[CH:31]=[CH:11][CH:10]=[CH:9][CH:14]=3)[CH:6]=2)=[N:25][CH:24]=1

Participants

5

Reactant 4

HCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 42580098rel-(1R,2R,3S,4S)-3-Aminobicyclo[2.2.1]hept-5-ene-2-carboxamide

Product 1

HCID 68781666HCID 68781666, compound

Procedure

The title compound was prepared as described in Example 1, substituting 1-(2-phenylethyl)-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-bromopyrimidine for 2,4-dichloro-5-fluoropyrimidine in Example 1A. 1H NMR (300 MHz, DMSO-d6) ppm 1.40 (d, J=8.82 Hz, 1H) 2.10 (d, J=8.48 Hz, 1H) 2.73 (s, 1H) 2.87 (s, 1H) 3.06 (t, J=7.29 Hz, 2H) 3.99-4.12 (m, 1H) 4.26 (t, J=7.29 Hz, 2H) 6.25 (d, J=8.48 Hz, 1H) 6.31-6.40 (m, 1H) 7.15 (d, J=6.78 Hz, 2H) 7.20-7.30 (m, 4H) 7.53 (s, 1H) 7.64 (s, 2H) 7.78 (s, 1H) 7.94 (s, 1H) 9.09 (s, 1H); MS (ESI(+)) m/e 494 (M+H)+.

Sources & evidence

ORD record
ord-0da0124283134aaead53a003f9c74f77
Source dataset
uspto-grants-2013_04
Patent number
US08426408B2

Reaction notes

Loading…