Lithium iodide → HCID 54712214, compound

HRID 720286Notes

Reaction equation

HRID 720286 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][S:20]2(=[O:26])=[O:25])[N:12]([CH3:18])[C:13](=[O:17])[C:14]=1[O:15]C)=[O:8].[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:6][C:7]([C:9]2[N:10]=[C:11]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][S:20]3(=[O:25])=[O:26])[N:12]([CH3:18])[C:13](=[O:17])[C:14]=2[OH:15])=[O:8])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 58739071HCID 58739071, compound

Product 1

HCID 54712214HCID 54712214, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

Reaction of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid 3,4-dichloro-benzylamide (0.160 g, 0.337 mmol) in 2,4,6-collidine with lithium iodide gave 0.118 g (76% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.70–1.85 and 2.06–2.15 (2×1H, 2 m, CH2), 2.3–2.4 (2H, m, CH2), 3.2–3.33 (2H, m, CH2 ), 3.64 (3H, s, NCH3), 3.7–3.85 (2H, m, CH2), 4.58 (2H, AB part of ABX system, JAB=15.5 Hz, Δν=49.6 Hz, JAX=6.6 Hz, JBX=6.1 Hz, NCH2), 7.18 (1H, broad dd, aromatic), 7.42 (1H, broad d, aromatic), 7.45 (1H, d, J=8.1 Hz, aromatic, 7.57 (1H, broad NH). HRMS (FAB POS) calculated for C17H19Cl2N4O5S [M+H+]: 461.045322. found: 461.045599.

Sources & evidence

ORD record
ord-e225515cce964b60a07216e4e2986f56
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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