Diisopropylethylamine → HCID 57345437, compound

HRID 1808851Notes

Reaction equation

HRID 1808851 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[F:20])[C:14]([OH:16])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:43][CH:44]([CH3:55])[CH2:45][C@H:46]([NH:53][CH3:54])[CH2:47][N:48]1[CH2:51][CH:50]([OH:52])[CH2:49]1>C(Cl)Cl>[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[F:20])[C:14]([N:53]([C@@H:46]([CH2:45][CH:44]([CH3:55])[CH3:43])[CH2:47][N:48]1[CH2:49][CH:50]([OH:52])[CH2:51]1)[CH3:54])=[O:16]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 991663,4-Difluorobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67773964HCID 67773964, compound

Product 1

HCID 57345437HCID 57345437, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (0.252 mL, 1.45 mmol) was added to a stirred suspension of 3,4-difluorobenzoic acid (76 mg, 0.48 mmol) and TBTU (155 mg, 0.48 mmol) in DCM (2 mL) at rt. The suspension was stirred for 3 min. A solution of (S)-1-(4-methyl-2-(methylamino)pentyl)azetidin-3-ol (Compound G2.4) (100 mg, 0.48 mmol) in DCM (1 mL) was added and the reaction was stirred at rt overnight. The reaction was washed with an 8% aq. solution of NaHCO3 (1.5 mL). The organic layer was concentrated and purified by preparative HPLC affording the title compound (102 mg, 65%). Mixture of rotamers:

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. washThe reaction was washed with an 8% aq. solution of NaHCO3 (1.5 mL)
  3. concentrationThe organic layer was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-75ae8e9b2114469d9f5c054b340d08c1
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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