Cyclohexanemethylamine → HCID 18790608, compound

HRID 1107002Notes

Reaction equation

HRID 1107002 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:17]=[CH:16][C:10]([O:11][CH2:12][C:13]([OH:15])=O)=[CH:9][CH:8]=2)[N:6]=1.[CH:18]1([CH2:24][NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]([NH:25][CH2:24][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:15])=[CH:16][CH:17]=2)[N:6]=1

Participants

7

Reactant 4

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3074898Acetic acid, (4-(2-amino-4-thiazolyl)phenoxy)-

Product 1

HCID 18790608HCID 18790608, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of example 3 (358 mg, 1.0 mmol) in DMF (10 mL) were added successively cyclohexanemethylamine (130 μL, 1.0 mmol), DIPEA (700 μL, 4.0 mmol) and TBTU (321 mg, 1.0 mmol). The resulting mixture was stirred at room temperature for 18 h and then diluted with EtOAc. The mixture was washed with a saturated aqueous solution of NaHCO3 and then brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 4:1, EtOAc:hexane) to afford the title compound (300 mg, 87% yield) as a white solid: M.p. 145-147°; 1H NMR (400 MHz, DMSO-d6) δ 8.00 (broad t, J=6.0 Hz, 1H), 7.71 (d, J=8.7 Hz, 2H), 6.98 (s, 2H), 6.94 (d, J=8.7 Hz, 2H), 6.84 (s, 1H), 4.48 (s, 2H), 2.97 (t, J=6.4 Hz, 2H), 0.82-1.66 (m, 11H); MS (FAB) m/z 346 (MH)+. Anal. Calcd for C18H23N3O2S: C, 62.58; H, 6.71; N, 12.16. Found: C, 62.48; H, 6.74; N, 12.17.

Workup

  1. washThe mixture was washed with a saturated aqueous solution of NaHCO3
  2. dry with materialbrine, dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (SiO2, 4:1, EtOAc:hexane)

Sources & evidence

ORD record
ord-c3a77fb9a0f14067b0db95a838f33a58
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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