4-((S)-1-Amino-2-azetidin-1-yl-ethyl)-2-chloro-benzonitrile hydrochloride → HCID 76073175, compound

HRID 60003Notes

Reaction equation

HRID 60003 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:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[CH:24]=1)[CH2:18][N:19]1[CH2:22][CH2:21][CH2:20]1>>[N:19]1([CH2:18][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)[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[C:25]([Cl:31])[CH:24]=2)[CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 901904684-((S)-1-Amino-2-azetidin-1-yl-ethyl)-2-chloro-benzonitrile hydrochlorideHCID 1785136844-oxo-1H-pyrido[3,2-d]pyrimidine-8-carboxamide

Product 1

HCID 76073175HCID 76073175, compound

Procedure

Compound 47 was prepared following general synthesis scheme 7 wherein 4-hydroxypyrido[3,2-d]pyrimidine-8-carboxamide (G) was reacted with 4-((S)-1-Amino-2-azetidin-1-yl-ethyl)-2-chloro-benzonitrile hydrochloride to give the title compound as a white solid. LC/MS [409 (M+H)]; 1H NMR (400 MHz, DMSO-d6) δ 9.90 (s, 1H), 9.16 (d, 1H), 9.03 (d, 1H), 8.56 (s, 1H), 8.40 (d, 1H), 8.18 (s, 1H), 7.93 (d, 1H), 7.66 (d, 1H), 5.35 (s, 1H), 3.27-2.97 (m, 2H), 2.88 (d, 2H), 2.01-1.83 (m, 4H).

Workup

  1. customCompound 47 was prepared

Sources & evidence

ORD record
ord-8b1d1ac3ee194120bf64ba5d3954bfad
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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