4-Methylmorpholine → HCID 178460985, compound

HRID 1160260Notes

Reaction equation

HRID 1160260 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[C:10]1=[O:31].CCN=C=NCCCN(C)C.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.Cl.[F:71][C:72]([F:80])([F:79])[CH:73]1[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([N:76]3[CH2:77][CH2:78][CH:73]([C:72]([F:80])([F:79])[F:71])[CH2:74][CH2:75]3)=[O:40])=[CH:37][CH:38]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][Si:21]([CH:22]([CH3:23])[CH3:24])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:26])[CH3:27])[CH2:16][CH2:15]2)[C:10]1=[O:31]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 178460988HCID 178460988, compound

Product 1

HCID 178460985HCID 178460985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mix 3′,5′-Dichloro-4′-[(R)-2-oxo-trans-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid (Preparation 21) (0.94 g, 1.52 mmol), EDCI (0.358 g, 1.83 mmol), N-methylmorpholine (0.50 mL, 4.57 mmol), HOBT (0.511 g, 1.52 mmol) and 4-trifluoromethyl-piperidine hydrochloride (0.466 g, 3.05 mmol) in CH2Cl2 (15 mL). Stir for 12 hours at room temperature. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with NaHCO3, brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography receive 0.586 g (51%) of the title compound: Mass spectrum (apci) m/z=753 (M+H).

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with NaHCO3, brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-1d12f1bfab65493bb742cb513b907617
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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