Tert-butyl 3-amino-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylate → 4-((4-(3-(Trifluoromethyl)phenyl)piperidin-3-yl)amino)pyrido[3,2-d]pyrimidine-8-carboxamide

HRID 59982Notes

Reaction equation

HRID 59982 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.[NH2:15][CH:16]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1>>[F:31][C:28]([F:29])([F:30])[C:24]1[CH:23]=[C:22]([CH:21]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[NH:15][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)[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 43811007Tert-butyl 3-amino-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylateHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 760730264-((4-(3-(Trifluoromethyl)phenyl)piperidin-3-yl)amino)pyrido[3,2-d]pyrimidine-8-carboxamide

Procedure

Compound 24 was prepared following general synthesis scheme 9 wherein 4-hydroxy-pyrido[3,2-d]pyrimidine-8-carboxylic acid amide was reacted with tert-butyl 3-amino-4-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate to give the title compound. LC-MS [417 (M+H)], 1H NMR (400 MHz, DMSO-d6) δ 9.78 (d, 1H), 9.06 (d, 1H), 9.03-8.95 (m, 1H), 8.90 (d, 1H), 8.88-8.73 (m, 1H), 8.50 (s, 1H), 8.32 (d, 1H), 8.16 (d, 1H), 7.62 (s, 1H), 7.56 (q, 1H), 7.43 (d, 2H), 5.22-5.02 (m, 1H), 3.60-3.38 (m, 3H), 3.14 (q, 1H), 2.99 (q, 1H), 2.54 (d, 1H), 2.08 (dt, 2H).

Workup

  1. customCompound 24 was prepared

Sources & evidence

ORD record
ord-04ad052ef7164dadb37ecdb6f1f11a4c
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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