Triethylamine → HCID 18761418, compound

HRID 431740Notes

Reaction equation

HRID 431740 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][OH:24])=[C:14]([NH:25][C:26]([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][C:33]([O:37][CH3:38])=[CH:32][CH:31]=3)=[O:27])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>C1COCC1.C(Cl)Cl>[CH3:46][S:47]([O:24][CH2:23][CH2:22][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])=[CH:13][C:14]=1[NH:25][C:26]([C:28]1[NH:29][C:30]2[C:35]([CH:36]=1)=[CH:34][C:33]([O:37][CH3:38])=[CH:32][CH:31]=2)=[O:27])(=[O:49])=[O:48]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18761436HCID 18761436, compound

Product 1

HCID 18761418HCID 18761418, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (0.4 g, 0.78 mmol) and triethylamine (0.44 mL, 3.14 mmol) in THF (20 mL) was added methanesulfonyl chloride (0.24 mL, 3.14 mmol) with ice bath and stirred for 1 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with H2O (10 mL) and saturated aqueous NaCl (20 mL), and then the organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica-gel column (30% AcOEt-Petroleum ether) to yield as a yellow foam 2-[4-(N-benzyloxycarbonylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethyl methanesulfonate (0.28 g, 61%): mp 160° C. (decomp.); 1H NMR (CDCl3, 500 MHz) δ 9.09 (brs, 1H), 8.36 (brs, 1H), 7.89 (d, 9.0, 1H), 7.87 (d, 9.0, 1H), 7.57 (t, 8.5, 1H), 7.48 (d, 7.5, 2H), 7.40 (t, 7.5, 2H), 7.34 (m, 2H), 7.17 (s, 1H), 7.13 (s, 1H), 7.00 (d, 8.5, 1H), 7.00 (d, 9.0, 1H), 4.70 (brs, 2H), 4.61 (t, 6.0, 2H), 4.50 (s, 2H), 3.88 (s, 3H), 3.54 (t, 6.0, 2H), 2.84 (s, 3H); ); FABMS (NBA) m/z 543 (M−CO2+), IR (neat) νmax 3400, 1643, 1591, 1530, 1479, 1453, 1351, 1231, 1213, 1173, 1142, 1076, 1031, 974, 947, 841, 805, 761, 734, 699 cm−1.

Workup

  1. washwashed with H2O (10 mL) and saturated aqueous NaCl (20 mL)
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column (30% AcOEt-Petroleum ether)

Sources & evidence

ORD record
ord-266013dcf5b34365994f8f1afe73f7c6
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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