4-Chlorobenzoic Acid → HCID 57345479, compound

HRID 1808846Notes

Reaction equation

HRID 1808846 reaction equation
CCN(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][CH2:53][CH3:54])[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][CH2:53][CH3:54])[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 67773496HCID 67773496, compound

Product 1

HCID 57345479HCID 57345479, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (0.275 mL, 1.58 mmol) was added to a stirred suspension of 4-chlorobenzoic acid (0.082 g, 0.53 mmol) and TBTU (0.169 g, 0.53 mmol) in DCM (1 mL) at rt. The suspension was stirred for 5 min. A solution of (S)-1-(2-(methylamino)hexyl)azetidin-3-ol (Compound G2.2) (0.11 g, 0.53 mmol) in DCM (1 mL) was added and the reaction was stirred at rt overnight. The reaction mixture was washed with an 8% aq. sol. of NaHCO3 (2 mL). The organic layer was dried through a phase separator and the solvent was removed in vacuo. Purification by preparative HPLC afforded the title compound (51 mg, 30%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.75-0.80, 0.82-0.87, 0.91-0.99, 1.02-1.46, 2.31-2.39, 2.44-2.62, 2.65-2.73, 3.16-3.53, 3.99-4.17, 4.36-4.48, 5.23, 7.30-7.33, 7.35-7.39, 7.45-7.49. Total number of protons in spectrum: 25. HRMS (M+H)+: calculated 325.1683. found 325.169

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. washThe reaction mixture was washed with an 8% aq. sol. of NaHCO3 (2 mL)
  3. customThe organic layer was dried through a phase separator
  4. customthe solvent was removed in vacuo
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-23c7fc38b64f49bda53bcce1f341d858
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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