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 1521884Notes

Reaction equation

HRID 1521884 reaction equation
[Na].[F:2][C:3]1[C:8]([F:9])=[C:7]([C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:14]1[N:15]=[C:16]([NH:19][C:20](=[O:35])[CH2:21][C:22]2[C:30]3[C:29](=[O:31])[N:28]([CH3:32])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=3[S:24][N:23]=2)[S:17][CH:18]=1.[P:36]([O-:40])([O-:39])([O-:38])=[O:37].[CH3:41]C(C)([O-])C.[Na+]>C1COCC1.CCCCCC>[P:36]([OH:40])([OH:39])([O:38][CH2:41][N:15]1[C:14]([C:4]2[CH:5]=[CH:6][C:7]([C:10]([F:12])([F:11])[F:13])=[C:8]([F:9])[C:3]=2[F:2])=[CH:18][S:17][C:16]1=[N:19][C:20](=[O:35])[CH2:21][C:22]1[C:30]2[C:29](=[O:31])[N:28]([CH3:32])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=2[S:24][N:23]=1)=[O:37]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 5360545SodiumHCID 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)acetamide2×

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

Sodium salt 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: 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-b1c42f61be0f420e85a471849b3298d2
Source dataset
uspto-grants-2015_07
Patent number
US09073955B2

Reaction notes

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