4-Chlorobenzoic Acid → HCID 57345459, compound

HRID 1808824Notes

Reaction equation

HRID 1808824 reaction equation
C(N(C(C)C)C(C)C)C.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:42][NH:43][C@@H:44]([CH2:51][CH2:52][CH3:53])[CH2:45][N:46]1[CH2:49][CH:48]([OH:50])[CH2:47]1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:43]([C@@H:44]([CH2:51][CH2:52][CH3:53])[CH2:45][N:46]2[CH2:47][CH:48]([OH:50])[CH2:49]2)[CH3:42])=[O:17])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67775012HCID 67775012, compound

Product 1

HCID 57345459HCID 57345459, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-ethyl-N-isopropylpropan-2-amine (1.580 mL, 9.07 mmol) was added to a stirred suspension of 4-chlorobenzoic acid (0.473 g, 3.02 mmol) and TBTU (0.971 g, 3.02 mmol) in DCM (10 mL) at rt. The suspension was stirred for about 5 min before a solution of (S)-1-(2-(methylamino)pentyl)azetidin-3-ol (Compound J4) (0.62 g, 3.02 mmol) in DCM (3 mL) was added. The reaction was stirred at rt overnight. The reaction mixture was washed with an 8% aq. sol. of NaHCO3 (20 mL). The organic layer was dried through a phase separator and concentrated on the rotary evaporator. The residue was purified by preparative HPLC affording the title compound (0.760 g, 81%) as an oil. Mixture of rotamers: 1H NMR (400 MHz, CD3OD) δ 0.80-0.88, 0.94-1.01, 1.09-1.65, 2.39-2.53, 2.62-2.99, 3.28-3.62, 3.65-3.76, 4.22-4.39, 4.64-4.76, 7.39-7.52. HRMS (M+H)+: calculated 311.1526. found 311.1539.

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with an 8% aq. sol. of NaHCO3 (20 mL)
  3. customThe organic layer was dried through a phase separator
  4. concentrationconcentrated on the rotary evaporator
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6e77aaa49ce34d63b0bab87e02bd310e
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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