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

HRID 60011Notes

Reaction equation

HRID 60011 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:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([C:41]([F:44])([F:43])[F:42])[CH:35]=1)[CH2:17][N:18]([CH:31]([CH3:33])[CH3:32])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O>>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([C@H:16]([NH:15][C:2]2[C:3]3[N:11]=[CH:10][CH:9]=[C:8]([C:12]([NH2:14])=[O:13])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:17][NH:18][CH:31]([CH3:33])[CH3:32])=[CH:35][C:36]=1[C:41]([F:42])([F:43])[F:44]

Participants

3

Reactant 2

HCID 90190461N-[(S)-2-Amino-2-(4-chloro-3-trifluoromethyl-phenyl)-ethyl]-N-isopropyl-4-nitro-benzenesulfonamideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760732214-[(S)-1-(4-Chloro-3-trifluoromethyl-phenyl)-2-isopropylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 55 was prepared following general synthesis scheme 7 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with N—[(S)-2-Amino-2-(4-chloro-3-trifluoromethyl-phenyl)-ethyl]-N-isopropyl-4-nitro-benzenesulfonamide to give the title compound as a white solid. LC/MS [454 (M+H)]; 1H NMR (400 MHz, DMSO-d6) δ 9.92 (s, 1H), 9.26 (s, 1H), 9.01 (d, 1H), 8.55 (s, 1H), 8.38 (d, 1H), 8.17 (s, 1H), 8.01 (s, 1H), 7.76 (d, 1H), 7.67 (d, 1H), 5.47 (s, 1H), 3.15 (d, 1H), 3.02 (s, 1H), 2.80-2.69 (m, 1H), 0.96 (dd, 6H).

Workup

  1. customCompound 55 was prepared

Sources & evidence

ORD record
ord-fb6b0e8f4c4c4b7789a497109d85fe65
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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