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Morpholine → HCID 86706367, compound

HRID 1396928
Notes
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Reaction equation

HRID 1396928 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:32][N:33]([CH:41]=[O:42])[O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C:8]([N:10]2[CH:14]([C:15]([NH:17][C:18]3[N:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2C(OCC=C)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCOCC1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([CH2:6][C@H:7]([CH2:32][N:33]([CH:41]=[O:42])[O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86706368HCID 86706368, compound

Product 1

HCID 86706367HCID 86706367, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Pd(Ph3P)4 (23.77 mg, 0.021 mmol) was added to a solution of 2-propen-1-yl 2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-3-({[5-(methyloxy)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate (173 mg, 0.294 mmol) and morpholine (81 μl, 0.935 mmol) in dichloromethane (DCM) (4.1 ml). The mixture was stirred at ambient temperature for 30 min. The solvent was removed under reduced pressure to give a crude product which was purified by RP-HPLC to give (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-N-[5-(methyloxy)-2-pyrimidinyl]-3-pyrazolidine carboxamide (67 mg, 0.133 mmol, 45% yield). MS (ES+) m/z 505.2 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a crude product which
  3. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-7f4671e76d4f457dbbab4678660051dc
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901119B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes