4-Chlorobenzoic Acid → (S)-4-Chloro-N-(3-methyl-1-(pyrrolidin-1-yl)butan-2-yl)benzamide

HRID 1808788Notes

Reaction equation

HRID 1808788 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:42][CH:43]([CH3:52])[C@H:44]([NH2:51])[CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:51][C@@H:44]([CH:43]([CH3:52])[CH3:42])[CH2:45][N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 63184-Chlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22689455(S)-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine

Product 1

HCID 67773300(S)-4-Chloro-N-(3-methyl-1-(pyrrolidin-1-yl)butan-2-yl)benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chlorobenzoic acid (1.061 g, 6.78 mmol), TBTU (2.25 g, 7.01 mmol) and DIPEA (20.3 mmol) was mixed in DMF (25 mL). After 10 min was (S)-3-methyl-1-(pyrrolidin-1-yl)butan-2-amine (0.962 g, 6.16 mmol), which is commercially available, added. The resultant mixture was stirred at rt over night. The mixture was concentrated and the residue was purified by preparative HPLC to give the title compound (1.48 g, 82%). 1H NMR (400 MHz, CDCl3) δ 0.97, 1.80, 1.94-2.32, 2.47-2.76, 2.80-3.01, 4.13, 6.66, 7.41, 7.80. Total no of protons: 23. LCMS (M+H)+: 295.

Workup

  1. additionadded
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-5ce8fec5258341edb563d9894ae8601f
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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