Chloromethyl pivalate → HCID 57377443, compound

HRID 338177Notes

Reaction equation

HRID 338177 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([C:14]2[N:15]=[C:16]([NH:19][C:20](=[O:36])[CH2:21][C:22]3[C:30]4[C:29](=[O:31])[N:28]([CH3:32])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=4[O:24][C:23]=3[CH3:35])[S:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]([F:13])([F:12])[F:11].[C:37]([O:43][CH2:44]Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>CC(C)=O>[CH3:39][C:38]([CH3:41])([CH3:40])[C:37]([O:43][CH2:44][N:15]1[C:14]([C:5]2[CH:6]=[CH:7][C:8]([O:9][C:10]([F:13])([F:11])[F:12])=[C:3]([Cl:2])[CH:4]=2)=[CH:18][S:17][C:16]1=[N:19][C:20](=[O:36])[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[O:24][C:23]=1[CH3:35])=[O:42]

Participants

5

Reactant 3

HCID 87885Chloromethyl pivalateHCID 5360545SodiumHCID 46918165HCID 46918165, compound

Product 1

HCID 57377443HCID 57377443, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared by the reaction of sodium salt of N-{4-[3-chloro-4-(trifluoromethoxy)phenyl]-1,3-thiazol-2-yl}-2-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydrofuro[2,3-d]pyrimidin-5-yl)acetamide (2.0 g, 0.0036 mol) with chloromethyl pivalate (0.82 g, 0.005455 mol) in dry acetone (60 ml) to yield 390 mg of product as an off white solid. 1H NMR (300 MHz, CDCl3) δ 1.22 (s, 9H), 2.34 (s, 3H), 3.33 (s, 3H), 3.53 (s, 3H), 4.11 (s, 2H), 6.49 (s, 2H), 7.24 (s, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.79 (d, J=8.7 Hz, 1H), 7.98 (s, 1H). ESI-MS (m/z): 642.75 (M+H)+.

Sources & evidence

ORD record
ord-691a56cb8e3947f299b3ffaa53cce9c7
Source dataset
uspto-grants-2014_11
Patent number
US08889862B2

Reaction notes

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