4-[1-Azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amine → HCID 57461721, compound

HRID 1896655Notes

Reaction equation

HRID 1896655 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH:11]=[N:10][C:9]=2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:5]=[CH:4][N:3]=1.NC1N=C(C2N(C3CN(C(OC(C)(C)C)=O)C3)C=NC=2C2C=CC(F)=CC=2)C=CN=1.N1CC(N2C(C3C=CN=C(N)N=3)=C(C3C=CC(F)=CC=3)N=C2)C1>>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:9]2[N:10]=[CH:11][N:12]([CH:13]3[CH2:17][CH2:16][NH:15][CH2:14]3)[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 574617124-[1-Azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amineHCID 57461719HCID 57461719, compoundHCID 57461720HCID 57461720, compound

Product 1

HCID 57461721HCID 57461721, compound

Procedure

tert-Butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]pyrrolidine-1-carboxylate (C17) was converted to the product using the same conditions employed for transformation of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C4) to 4-[1-azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amine (C5) in Example 1. The product was obtained as a solid. Yield: 3.3 g, 10 mmol, 69%. LCMS m/z 325.6 (M+1). 1H NMR (400 MHz, CD3OD) δ 2.09-2.18 (m, 1H), 2.32-2.41 (m, 1H), 2.98-3.11 (m, 2H), 3.16-3.23 (m, 1H), 3.3 (m, 1H, assumed; obscured by solvent signal), 5.26 (m, 1H), 6.42 (d, J=5.1 Hz, 1H), 7.07 (dd, J=8.8, 8.8 Hz, 2H), 7.42 (dd, J=8.7, 5.4 Hz, 2H), 8.05 (s, 1H), 8.14 (d, J=5.3 Hz, 1H).

Workup

  1. customThe product was obtained as a solid

Sources & evidence

ORD record
ord-892426f948724d7183e1f229eff13197
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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