Sodium hydride → HCID 53832659, compound

HRID 1954304Notes

Reaction equation

HRID 1954304 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[CH:16]=4)[C:4]=2[C:3]=1[CH3:27])[CH:12]=[CH:11][CH:10]=[CH:9]3.[H-].[Na+].[CH3:30][S:31][C:32]1[N:37]=[C:36]([C:38]2[S:42][C:41]([S:43](Cl)(=[O:45])=[O:44])=[CH:40][CH:39]=2)[CH:35]=[CH:34][N:33]=1>>[CH:22]1([C:17]2[CH:16]=[C:15]([C:14]3[C:4]4[C:3]([CH3:27])=[C:2]([CH3:1])[S:6][C:5]=4[CH:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)[CH:20]=[CH:19][C:18]=2[O:21][S:43]([C:41]2[S:42][C:38]([C:36]3[CH:35]=[CH:34][N:33]=[C:32]([S:31][CH3:30])[N:37]=3)=[CH:39][CH:40]=2)(=[O:44])=[O:45])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27369955-(2-(Methylthio)-4-pyrimidinyl)-2-thiophenesulfonyl chlorideHCID 184307052-Cyclopentyl-4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol

Product 1

HCID 53832659HCID 53832659, compoundYield 58%

Procedure

The title compound was prepared according to the procedure in Example 10, step 1, using 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenol (0.300 g, 0.805 mmol), 60% sodium hydride/mineral oil (0.032 g, 0.805 mmol) and commercial 5-[2-(methylthio)pyrimidin-4-yl]thiophene-2-sulphonyl chloride (0.272 g, 0.886 mmol). Purification on Biotage KP-Sil eluting with 25% EtOAc/pet. ether gave 0.299 g (58%) of the title compound as a yellow solid, mp 100-110° C. 1H NMR (DMSO-d6) δ 1.32-1.37 (m, 2 H), 1.45-1.65 (m, 8 H), 1.84-1.90 (m, 1 H), 2.37 (s, 3 H), 2.55 (s, 3 H), 3.15 (quintet, 1 H), 7.25-7.38 (m, 5 H), 7.44 (ddd, 1 H), 7.90 (d, 1 H), 7.96 (d, 1 H), 8.08 (d, 1 H), 8.27 (d, 1 H), 8.48 (s, 1 H), 8.77 (d, 1 H). mass spectrum (+APCI) m/z 643 (M+H). C34H30N2O3S4 : C, 63.52; H, 4.70; N, 4.36. Found: C, 63.18; H, 4.46; N, 4.19.

Workup

  1. customThe title compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 25% EtOAc/pet. ether

Sources & evidence

ORD record
ord-ec4764c984aa4b6a9aaf6dc38eca9832
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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