Hydrochloric Acid → HCID 22144262, compound

HRID 1824730Notes

Reaction equation

HRID 1824730 reaction equation
[CH2:1]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](C(O)=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C[N:21]([CH3:35])C1C2C(=CC=CC=2N(C)C)C=CC=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])=CC=1.[C:53]1([NH2:63])[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[CH:55][CH:54]=1.Cl>C1COCC1.C(Cl)Cl>[C:53]1([NH:63][C:35]([NH:21][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[O:43])[C:62]2[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=2)[CH:56]=[CH:55][CH:54]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 86401-NaphthylamineHCID 88675Proton spongeHCID 199401P,P-Diphenylphosphinic azideHCID 22144274HCID 22144274, compound

Product 1

HCID 22144262HCID 22144262, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-pentyloxy-naphthalene-1-carboxylic acid (103 mg, 0.4 mmol) and 1,8-bis(dimethylamino)naphthalene (86 mg, 0.4 mmol) in THF (0.8 mL) is stirred at room temperature for 30 min. After addition of DPPA (86 μL, 0.4 mmol) and 1-naphthylamine (229 mg, 1.6 mmol) the mixture is heated at 100° C. for 6 h, distributed between 2M HCl (8 mL) and DCM (2×8 mL). The combined organic phases are washed with 1 M Na2CO3 and water, dried over Na2SO4 and concentrated. Flash chromatography (cyclohexane/acetone) yields 78 mg (49%) of brownish crystals.

Workup

  1. washThe combined organic phases are washed with 1 M Na2CO3 and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e5fd8a3295854397a104a9d1a72b72cb
Source dataset
uspto-grants-2006_05
Patent number
US07045533B2

Reaction notes

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