Sodium hydride → Mubritinib

HRID 2084392Notes

Reaction equation

HRID 2084392 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][C:21]1[N:22]=[C:23](/[CH:26]=[CH:27]/[C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[O:24][CH:25]=1>>[F:37][C:34]([F:35])([F:36])[C:31]1[CH:32]=[CH:33][C:28](/[CH:27]=[CH:26]/[C:23]2[O:24][CH:25]=[C:21]([CH2:20][O:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[N:2]4)=[CH:15][CH:14]=3)[N:22]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 98571264-(chloromethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazoleHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenol

Product 1

HCID 6444692MubritinibYield 88.5%

Procedure

Using 4-[4-(1H-1,2,3-triazol-1-yl)butyl]phenol (152 mg), 65% oily sodium hydride (28 mg) and 4-(chloromethyl)-2-{(E)-2-[4-(trifluoromethyl)phenyl]ethenyl}-1,3-oxazole (212 mg), the same reaction as Example 2 was carried out to yield the titled compound (290 mg).

Workup

  1. customthe same reaction as Example 2

Sources & evidence

ORD record
ord-0321a4c1fb164ac69e1266da44c9a0c1
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

Loading…