(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → 3-(2-aminopyrimidin-4-yl)-5-[(3R)-3-hydroxy-3-(5-methyl-1,2-oxazol-3-yl)but-1-yn-1-yl]-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

HRID 1398640Notes

Reaction equation

HRID 1398640 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14](Br)[CH:15]=[CH:16][C:11]=3[N:10]([CH3:18])[C:9]2=[O:19])[CH:5]=[CH:4][N:3]=1.[CH3:20][C:21]1[O:25][N:24]=[C:23]([C@:26]([OH:30])([C:28]#[CH:29])[CH3:27])[CH:22]=1>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[C:14]([C:29]#[C:28][C@@:26]([OH:30])([C:23]4[CH:22]=[C:21]([CH3:20])[O:25][N:24]=4)[CH3:27])[CH:15]=[CH:16][C:11]=3[N:10]([CH3:18])[C:9]2=[O:19])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 681816083-(2-aminopyrimidin-4-yl)-5-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

Product 1

HCID 601648513-(2-aminopyrimidin-4-yl)-5-[(3R)-3-hydroxy-3-(5-methyl-1,2-oxazol-3-yl)but-1-yn-1-yl]-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

Procedure

The title compound was prepared by the method described in Step 2 of Example 142-b by reacting 3-(2-aminopyrimidin-4-yl)-5-bromo-1-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one with (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol: 1H NMR (500 MHz, DMSO) delta 1.82 (3H, s), 2.40 (3H, s), 3.38 (3H, s), 6.38 (1H, s), 6.44 (1H, s), 6.97 (2H, s), 7.33-7.22 (2H, m), 7.42 (1H, d, J=5.6 Hz), 8.32 (1H, d, J=5.6 Hz), 8.38 (1H, s); LC-MS: m/z=+391 (M+H)+.

Sources & evidence

ORD record
ord-b61157f220cc43f5934c2f95dee7ae94
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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