4-Methylmorpholine → HCID 67775126, compound

HRID 1808827Notes

Reaction equation

HRID 1808827 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[CH:41]1([C:44]2([OH:55])[CH2:47][N:46]([CH2:48][C@H:49]([CH:52]3[CH2:54][CH2:53]3)[NH:50][CH3:51])[CH2:45]2)[CH2:43][CH2:42]1.[OH-].[K+]>C(Cl)Cl>[CH:52]1([C@H:49]([N:50]([CH3:51])[C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=2)[CH2:48][N:46]2[CH2:45][C:44]([CH:41]3[CH2:42][CH2:43]3)([OH:55])[CH2:47]2)[CH2:53][CH2:54]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14797Potassium HydroxideHCID 2428284-Fluoro-3-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67773304HCID 67773304, compound

Product 1

HCID 67775126HCID 67775126, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-3-methylbenzoic acid (0.102 g, 0.66 mmol), TBTU (0.248 g, 0.77 mmol) and NMM (0.063 mL, 0.58 mmol) was mixed in DCM (10 mL). After 10 min at rt was (S)-3-cyclopropyl-1-(2-cyclopropyl-2-(methylamino)ethyl)azetidin-3-ol (Compound L2) (0.116 g, 0.55 mmol) added. The resultant mixture was stirred at rt for 48 h. To the mixture was 1.4 N KOH (5 mL) added. The organic phase was isolated, filtered through a phase separator and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (96 mg, 50%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.09-0.14, 0.22-0.70, 1.01, 1.18, 2.30, 2.52-2.55, 2.72-3.10, 3.20, 3.72, 5.12, 7.15-7.44. Total no of protons: 27. HRMS (M+H)+: calculated 347.2135. found 347.2124.

Workup

  1. additionadded
  2. customThe organic phase was isolated
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a07a01351dcf4c3eaf605fbb85535378
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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