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

HRID 60010Notes

Reaction equation

HRID 60010 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:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([F:42])[CH:36]=1)[CH2:18][N:19]([CH:32]([CH3:34])[CH3:33])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O>>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([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][CH:32]([CH3:33])[CH3:34])=[CH:36][C:37]=1[F:42]

Participants

3

Reactant 2

HCID 90190258N-[(S)-2-Amino-2-(4-chloro-3-fluoro-phenyl)-ethyl]-N-isopropyl-4-nitro-benzenesulfonamide hydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760732204-[(S)-1-(4-Chloro-3-fluoro-phenyl)-2-isopropylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 54 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-fluoro-phenyl)-ethyl]-N-isopropyl-4-nitro-benzenesulfonamide hydrochloride to give the title compound as a white solid. LC/MS [404 (M+H)].

Workup

  1. customCompound 54 was prepared

Sources & evidence

ORD record
ord-c627d3ab20c64814a7c1fe2cd5d42e67
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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