(S)-1-(4-Chloro-3-fluoro-phenyl)-N2,N2-dimethyl-ethane-1,2-diamine hydrochloride → 4-[(S)-1-(4-Chloro-3-fluoro-phenyl)-2-dimethylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

HRID 60009Notes

Reaction equation

HRID 60009 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.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH2:28])[CH2:24][N:25]([CH3:27])[CH3:26])=[CH:19][C:18]=1[F:29]>>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH:28][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)[CH2:24][N:25]([CH3:27])[CH3:26])=[CH:19][C:18]=1[F:29]

Participants

3

Reactant 2

HCID 90190221(S)-1-(4-Chloro-3-fluoro-phenyl)-N2,N2-dimethyl-ethane-1,2-diamine hydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760732194-[(S)-1-(4-Chloro-3-fluoro-phenyl)-2-dimethylamino-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide

Procedure

Compound 53 was prepared following general synthesis scheme 7 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with (S)-1-(4-Chloro-3-fluoro-phenyl)-N2,N2-dimethyl-ethane-1,2-diamine hydrochloride to give the title compound as a white solid. LC/MS [390 (M+H)]; 1H NMR (400 MHz, Acetonitrile-d3) δ 10.34 (s, 1H), 8.96 (d, 1H), 8.49 (d, 2H), 8.35 (s, 1H), 7.46 (t, 1H), 7.35 (d, 1H), 7.28 (d, 1H), 6.62 (s, 1H), 5.26 (d, 1H), 2.93 (t, 1H), 2.60 (dd, 1H), 2.29 (s, 6H).

Workup

  1. customCompound 53 was prepared

Sources & evidence

ORD record
ord-7ac0f42943ee4b208d63f0d6d260e928
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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