(S)-2-(Azetidin-1-yl)-1-(4-chloro-3-(trifluoromethyl)phenyl)ethan-1-amine dihydrochloride → 4-[(S)-2-Azetidin-1-yl-1-(4-chloro-3-trifluoromethyl-phenyl)-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxamide

HRID 59998Notes

Reaction equation

HRID 59998 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.[N:17]1([CH2:21][C@H:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=2)[NH2:23])[CH2:20][CH2:19][CH2:18]1>>[N:17]1([CH2:21][C@@H:22]([NH:23][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)[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:32])([F:33])[F:34])[CH:25]=2)[CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 90190614(S)-2-(Azetidin-1-yl)-1-(4-chloro-3-(trifluoromethyl)phenyl)ethan-1-amine dihydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760731384-[(S)-2-Azetidin-1-yl-1-(4-chloro-3-trifluoromethyl-phenyl)-ethylamino]-pyrido[3,2-d]pyrimidine-8-carboxamide

Procedure

Compound 41 was prepared following general synthesis scheme 8 wherein 4-hydroxy-pyrido[3,2-d]pyrimidine-8-carboxylamide (G) was reacted with (S)-2-(azetidin-1-yl)-1-(4-chloro-3-(trifluoromethyl)phenyl)ethanamine dihydrochloride to give the title compound as a off-white solid. LC/MS [451 (M+H)]; 1H NMR (400 MHz, DMSO-d6) δ 9.93 (s, 1H), 9.20 (s, 1H), 9.01 (d, 1H), 8.56 (d, 1H), 8.39 (dd, 1H), 8.20 (d, 1H), 8.05 (s, 1H), 7.80 (d, 1H), 7.68 (d, 1H), 5.38 (t, 1H), 3.11 (ddd, 5H), 2.84 (dd, 1H), 1.93 (p, 2H). IC50 p70S6K: 1.6 nM, Akt: 11 nM

Workup

  1. customCompound 41 was prepared

Sources & evidence

ORD record
ord-cacc33615fac4de4915dc3a2a5125166
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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