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

HRID 59988Notes

Reaction equation

HRID 59988 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:34]1[CH:39]=[CH:38][C:37]([F:40])=[C:36]([Br:41])[CH:35]=1)[CH2:18][N:19]([CH2:32][CH3:33])S(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O>>[Br:41][C:36]1[CH:35]=[C:34]([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][CH2:32][CH3:33])[CH:39]=[CH:38][C:37]=1[F:40]

Participants

3

Reactant 2

HCID 90190066N-[(S)-2-Amino-2-(3-bromo-4-fluoro-phenyl)-ethyl]-N-ethyl-4-nitro-benzenesulfonamide hydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760730624-[(S)-1-(3-Bromo-4-fluoro-phenyl)-2-ethylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 30 was prepared following general synthesis scheme 8 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with N—[(S)-2-Amino-2-(3-bromo-4-fluoro-phenyl)-ethyl]-N-ethyl-4-nitro-benzenesulfonamide hydrochloride to give the title compound as a white solid. LC/MS [434 (M+H)]; 1H NMR (400 MHz, DMSO-d6) δ 9.90 (s, 1H), 9.36 (s, 1H), 9.02 (d, J=4.5 Hz, 1H), 8.60 (s, 1H), 8.40 (d, J=4.4 Hz, 1H), 8.18 (s, 1H), 7.87 (d, J=4.9 Hz, 1H), 7.53 (d, J=5.5 Hz, 1H), 7.35 (t, J=8.7 Hz, 1H), 5.78-5.51 (m, 1H), 3.55-3.36 (m, 1H), 3.23-3.10 (m, 1H), 2.93-2.69 (m, 2H), 1.08 (t, J=7.0 Hz, 3H).

Workup

  1. customCompound 30 was prepared

Sources & evidence

ORD record
ord-f341ff09241d4579945d52017d1144f3
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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