4-Methylmorpholine → HCID 67773174, compound

HRID 1808829Notes

Reaction equation

HRID 1808829 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[CH:41]1([C@H:44]([NH:51][CH3:52])[CH2:45][N:46]2[CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:43][CH2:42]1.[OH-].[K+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([N:51]([C@@H:44]([CH:41]1[CH2:43][CH2:42]1)[CH2:45][N:46]1[CH2:47][CH2:48][CH2:49][CH2:50]1)[CH3:52])=[O:7]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 14797Potassium HydroxideHCID 5209893-Chloro-4-fluorobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67774025HCID 67774025, compound

Product 1

HCID 67773174HCID 67773174, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-4-fluorobenzoic acid (0.156 g, 0.89 mmol), TBTU (0.334 g, 1.04 mmol) and NMM (0.204 mL, 1.86 mmol) was mixed in DCM (10 mL). After 10 min at rt was (S)-1-cyclopropyl-N-methyl-2-(pyrrolidin-1-yl)ethanamine (Compound M3) (0.125 g, 0.74 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 (130 mg, 54%). Mixture of rotamers: 1H NMR (600 MHz, DMSO-d6) δ 0.03, 0.16-0.62, 0.95, 1.50-1.74, 2.14-2.41, 2.47-2.51, 2.65-3.06, 3.84, 7.29, 7.46. Total no of protons: 22. HRMS (M+H)+: calculated 325.1483. found 325.1475.

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-91d5e6ad9c654eae8534ee9054d1892a
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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