N-[(S)-2-Amino-2-(4-methyl-3-trifluoromethyl-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide → 4-[(S)-2-Methylamino-1-(4-methyl-3-trifluoromethyl-phenyl)-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

HRID 60026Notes

Reaction equation

HRID 60026 reaction equation
O[C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:15][C@@H:16]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=1)[CH2:17][N:18]([CH3:31])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O>>[CH3:31][NH:18][CH2:17][C@@H:16]([NH:15][C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1)[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([C:39]([F:41])([F:40])[F:42])[CH:33]=1

Participants

3

Reactant 2

HCID 90190460N-[(S)-2-Amino-2-(4-methyl-3-trifluoromethyl-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760733574-[(S)-2-Methylamino-1-(4-methyl-3-trifluoromethyl-phenyl)-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 76 was prepared following general synthetic scheme 11 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with N—[(S)-2-Amino-2-(4-methyl-3-trifluoromethyl-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide. LC-MS [405 (M+1)]; 1H NMR (400 MHz, DMSO-d6) d 9.95 (d, J=3.4 Hz, 1H), 9.21 (d, J=8.5 Hz, 1H), 9.00 (d, J=4.6 Hz, 1H), 8.54 (s, 1H), 8.38 (d, J=4.5 Hz, 1H), 8.16 (d, J=3.5 Hz, 1H), 7.80 (s, 1H), 7.63 (d, J=7.9 Hz, 1H), 7.38 (d, J=8.1 Hz, 1H), 5.51 (s, 1H), 3.15 (dd, J=12.4, 8.4 Hz, 1H), 2.92 (dd, J=12.3, 5.5 Hz, 1H), 2.40 (s, 4H), 2.30 (s, 3H).

Sources & evidence

ORD record
ord-05b3b8fe5e9a46e7a4c0107f90c875e5
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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