4-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dione → 4-(2-(3-(S,S-dioxo-4-thiapiperidin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 1676258Notes

Reaction equation

HRID 1676258 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17](I)[S:18][C:11]=12)[NH2:5].[CH2:20]([N:23]1[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH2:25][CH2:24]1)[C:21]#[CH:22]>>[O:30]=[S:26]1(=[O:29])[CH2:27][CH2:28][N:23]([CH2:20][C:21]#[C:22][C:17]2[S:18][C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]3[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=3[F:1])[CH:16]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 27772654-(Prop-2-yn-1-yl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 673501714-(2-(3-(S,S-dioxo-4-thiapiperidin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 80.2%

Conditions

Temperature
50 °C

Procedure

Prepared from 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 50 mg, 0.13 mmol) and commercially available N-propargyl-S,S-dioxo-4-thiapiperidine (34 mg, 0.19 mmol) according to the procedure described for Example 6, Step B, except the reaction was heated at 50° C. for 5 hours. The crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]. The product was obtained as a white powder (45 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=6 Hz, 1H), 7.61 (s, 1H), 7.03 (t, J=9 Hz, 1H), 6.55 (m, 2H), 6.49 (m, 1H), 3.86 (br s, 2H), 3.72 (s, 2H), 3.17 (m, 8H).

Workup

  1. customThe crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]

Sources & evidence

ORD record
ord-8b52ffedbc134e1f8db165e8223b313e
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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