Morpholine → HCID 24949457, compound

HRID 390734Notes

Reaction equation

HRID 390734 reaction equation
[CH3:1][C:2]12[CH2:25][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][CH2:20][CH:19]([C:22](O)=[O:23])[CH2:18]4)=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:27])([CH3:26])[CH2:3]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[NH:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1>C1COCC1>[N:58]1([C:22]([CH:19]2[CH2:20][CH2:21][N:17]([C:14]3[CH:13]=[CH:12][C:11]([C:9]([N:7]4[CH2:27][C:4]5([CH3:26])[CH2:5][CH:6]4[CH2:25][C:2]([CH3:1])([CH3:8])[CH2:3]5)=[O:10])=[CH:16][CH:15]=3)[CH2:18]2)=[O:23])[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24950283HCID 24950283, compound

Product 1

HCID 24949457HCID 24949457, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-pyrrolidine-3-carboxylic acid (300 mg, 0.81 mmol, prepared as described in ex-ample 1) and HOBT (131 mg, 0.97 mmol) in dry THF (20 ml) was added EDAC (186 mg, 0.97 mmol). The resulting mixture was stirred for 10 min followed by addition of a mixture of DIPEA (219 μl, 1.22 mmol) and morpholine (85 μl, 0.97 mmol). The reaction mixture was stirred for an additional 16 hrs. and evaporated to dryness. The resulting residue was purified by preparative HPLC (Gilson) and pure fractions were collected and evaporated to dryness and dried in vacuo at 50° C. affording 250 mg (70%) of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred for an additional 16 hrs
  2. customand evaporated to dryness
  3. customThe resulting residue was purified by preparative HPLC (Gilson) and pure fractions
  4. customwere collected
  5. customevaporated to dryness
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-8971605b5a9e40199b1573f3b1f96f19
Source dataset
uspto-grants-2013_02
Patent number
US08383668B2

Reaction notes

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