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

HRID 60013Notes

Reaction equation

HRID 60013 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.Cl.[NH2:16][C@@H:17]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[C:35]([Cl:40])[CH:34]=1)[CH2:18][N:19]([CH3:32])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O>>[Cl:40][C:35]1[CH:34]=[C:33]([C@H:17]([NH:16][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)[CH2:18][NH:19][CH3:32])[CH:38]=[CH:37][C:36]=1[F:39]

Participants

3

Reactant 2

HCID 90190119N-[(S)-2-Amino-2-(3-chloro-4-fluoro-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide hydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760732234-[(S)-1-(3-Chloro-4-fluoro-phenyl)-2-methylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 57 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-(3-chloro-4-fluoro-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide hydrochloride to give the title compound as a white solid. LC/MS [376 (M+H)]; 1H NMR (400 MHz, Acetonitrile-d3) δ 10.31 (s, 1H), 8.93 (d, 1H), 8.46 (dd, 3H), 7.51 (d, 1H), 7.36 (s, 1H), 7.20 (t, 1H), 6.58 (s, 1H), 5.34 (dd, 1H), 3.11 (dd, 1H), 3.00 (dd, 1H), 2.37 (s, 3H).

Workup

  1. customCompound 57 was prepared

Sources & evidence

ORD record
ord-338a383d35f44f9980d3ccde2eb06c9b
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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