4-Methylmorpholine → HCID 59560116, compound

HRID 1177115Notes

Reaction equation

HRID 1177115 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([F:23])[CH:22]=1)[O:5][C:6]1[C:11]2[CH2:12][C:13]([CH3:16])([CH3:15])[O:14][C:10]=2[CH:9]=[C:8]([C:17]([OH:19])=O)[CH:7]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[CH3:52][N:53]1[CH:57]=[CH:56][C:55]([NH2:58])=[N:54]1>C(Cl)Cl>[CH3:52][N:53]1[CH:57]=[CH:56][C:55]([NH:58][C:17]([C:8]2[CH:7]=[C:6]([O:5][C:4]3[CH:20]=[C:21]([F:23])[CH:22]=[C:2]([F:1])[CH:3]=3)[C:11]3[CH2:12][C:13]([CH3:15])([CH3:16])[O:14][C:10]=3[CH:9]=2)=[O:19])=[N:54]1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1372541-Methyl-3-aminopyrazoleHCID 59560462HCID 59560462, compound

Product 1

HCID 59560116HCID 59560116, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (113b) (0.308 g, 0.00096 mol), EDCI (0.28 g, 0.0015 mol), HOBt (0.21 g, 0.0015 mol) and NMM (0.49 g, 0.0048 mol) in CH2Cl2 (15 mL) was added 1-methyl-1H-pyrazol-3-amine (0.11 g, 0.001 mol) in one portion. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aq. citric acid and then sat. NaHCO3. The organic phase was dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by prep. HPLC to give the title compound (95 mg, 51% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.82 (s, 1 H), 7.20 (m, 2 H), 7.03 (d, 2 H), 6.73 (s, 1 H), 6.42 (m, 3 H), 3.72 (s, 3 H), 2.84 (s, 2 H), 1.42 (s, 6 H); LCMS for C21H19F2N3O3 m/z 400.4 (M+H)+.

Workup

  1. washThe reaction mixture was washed with water, aq. citric acid
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customto give a brown oil
  5. customThe crude oil was purified by prep

Sources & evidence

ORD record
ord-195902783fee40a58e88283da2f97609
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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