Phosphate → [4-[2,3-Difluoro-4-(trifluoromethyl)phenyl]-2-{[(5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-d]pyrimidin-3-yl)acetyl]imino}-1,3-thiazol-3(2H)-yl]methyl dihydrogen phosphate

HRID 2045898Notes

Reaction equation

HRID 2045898 reaction equation
[P:1]([O-:5])([O-:4])([O-:3])=[O:2].[F:6][C:7]1[C:12]([F:13])=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[C:18]1[N:19]=[C:20]([NH:23][C:24](=[O:39])[CH2:25][C:26]2[C:34]3[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]([CH3:38])[C:29]=3[S:28][N:27]=2)[S:21][CH:22]=1.[CH3:40]C(C)([O-])C.[Na+]>C1COCC1.CCCCCC>[P:1]([OH:5])([OH:4])([O:3][CH2:40][N:19]1[C:18]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:16])([F:15])[F:17])=[C:12]([F:13])[C:7]=2[F:6])=[CH:22][S:21][C:20]1=[N:23][C:24](=[O:39])[CH2:25][C:26]1[C:34]2[C:33](=[O:35])[N:32]([CH3:36])[C:31](=[O:37])[N:30]([CH3:38])[C:29]=2[S:28][N:27]=1)=[O:2]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 23676156Sodium t-butoxideHCID 46928084N-{4-[2,3-difluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}-2-(5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-d]pyrimidin-3-yl)acetamide

Product 1

HCID 57377336[4-[2,3-Difluoro-4-(trifluoromethyl)phenyl]-2-{[(5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-d]pyrimidin-3-yl)acetyl]imino}-1,3-thiazol-3(2H)-yl]methyl dihydrogen phosphate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared according to the general procedure as described in step 1 of method B for the preparation of phosphate derivatives by the reaction of N-{4-[2,3-difluoro-4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}-2-(5,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydro[1,2]thiazolo[5,4-d]pyrimidin-3-yl)acetamide (1.95 g, 3.771 mmol) with sodium-tert-butoxide (0.362 g, 3.771 mmol) in dry THF (12 ml) and hexane (40 ml) to yield 2.00 g of product as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 3.22 (s, 3H), 3.48 (s, 3H), 3.98 (s, 2H), 7.25 (s, 1H), 7.59 (t, J=8.1 Hz, 1H), 8.03 (t, t, J=7.2 Hz, 1H).

Sources & evidence

ORD record
ord-33220b11dca64b17be6a6d1e11b8fb57
Source dataset
uspto-grants-2013_11
Patent number
US08592398B2

Reaction notes

Loading…