Tetrahydrofuran → HCID 178454285, compound

HRID 278606Notes

Reaction equation

HRID 278606 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:30])[CH:26]=4)[CH:21]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.O1CCCC1.[C:43]([O:47][C:48]([NH:50][C:51](=[N:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])SC)=[O:49])([CH3:46])([CH3:45])[CH3:44]>CO>[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]([CH:6]3[CH2:7][CH2:8][CH:3]([NH:2][C:51]([NH:50][C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:49])=[N:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:4][CH2:5]3)=[O:10])[CH2:16][CH2:15]1)(=[O:18])=[O:19])[CH:29]=[CH:28]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 22628032HCID 22628032, compound

Product 1

HCID 178454285HCID 178454285, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(4-aminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (220 mg) and triethylamine (232 mg) in methanol (10 ml)-tetrahydrofuran (10 ml) was added N,N′-di-tert-butoxycarbonyl-S-methylisothiourea (135 mg) and the solution was stirred at 40° C. for 24 hours. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give a colorless solid of the title compound (170 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d99fb77d2f9e481cb38786f671bd0808
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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