Diisopropylethylamine → HCID 86583724, compound

HRID 651525Notes

Reaction equation

HRID 651525 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]([O:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])(=[O:23])=[O:22])[CH:11]=2)[CH2:4][CH2:3]1.Cl.[C:32](=[NH:37])([O:34]CC)[CH3:33].C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:12]([OH:20])(=[O:34])[CH3:13].[C:32]([N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]([O:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])(=[O:22])=[O:23])[CH:11]=2)[CH2:4][CH2:3]1)(=[NH:37])[CH3:33]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)2×HCID 86583725HCID 86583725, compound

Product 1

HCID 86583724HCID 86583724, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 mg (0.214 mmol) of 2-chlorobenzenesulfonic acid 1-[(piperidin-4-yl)methoxy]naphthalen-3-yl ester hydrochloride, as prepared in the preceding step, in N,N-dimethylformamide (2 mL) containing 55 mg (0.45 mmol) of ethyl acetimidate hydrochloride and 125 μL of N,N-diisopropylethylamine was stirred at ambient temperature overnight. To the reaction mixture was added another 125 μL of N,N-diisopropylethylamine and 55 mg (0.45 mmol) of ethyl acetimidate hydrochloride. The reaction mixture was stirred for another 4 h. The reaction mixture was concentrated to dryness, quenched with 1 N sodium hydroxide (2 mL), extracted into methylene chloride, dried (K2CO3), and concentrated in vacuo. The residue was diluted with methylene chloride (1 mL), treated with 1 mL of glacial acetic acid and directly purified by preparative thin layer chromatography using methylene chloride/methanol/glacial acetic acid (93.6:6.5:0.5) as developing solvent to give the title compound. 1H-NMR (300 MHz, DMSO-d6) δ 8.14 (d, 1 H, J=8 Hz), 7.8-7.97 (m, 4 H), 7.50-7.59 (m, 3 H), 7.19 (s, 1 H), 6.68 (d, 1 H, J=2 Hz), 4.11 (d, 2 H, J=6 Hz), 3.92 (d, 2 H, J=6 Hz), 3.11 (t, 2 H, J=2.6 Hz), 2.2 (m, 1 H), 1.92 (d, 2 H), 1.75 (br s, 3 H), and 1.41 (q, 2 H). Mass spectrum (MALDI-TOF; α-cyano-4-hydroxycinnamic acid matrix) calcd. for C23H24ClN3O4S: 474.1 (M+H). Found: 473.8.

Workup

  1. stirringThe reaction mixture was stirred for another 4 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. customquenched with 1 N sodium hydroxide (2 mL)
  4. extractionextracted into methylene chloride
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with methylene chloride (1 mL)
  8. additiontreated with 1 mL of glacial acetic acid
  9. customdirectly purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-5935f28cd8de4522889ffdff702a50ab
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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