Dimethylformamide → HCID 59656423, compound

HRID 561331Notes

Reaction equation

HRID 561331 reaction equation
[CH:1]1([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][NH2:22])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]1([CH3:30])[C:24](Cl)=[CH:25][CH:26]=[CH:27][CH:28]=1.C(N(CC)CC)C.CN([CH:41]=[O:42])C>>[CH:1]1([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][NH:22][C:41](=[O:42])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH3:30])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 72382-ChlorotolueneHCID 8471TriethylamineHCID 59656442HCID 59656442, compound

Product 1

HCID 59656423HCID 59656423, compound

Procedure

To a solution of naphthalenyl methylamine 42 (100 mg, 0.32 mmol) in DMF (2 mL) was added o-tolylchloride (49 μL, 0.38 mmol) and triethylamine (88 μL, 0.63 mmol). The resultant solution was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified using HPLC to give the title compound (G-5) (30 mg) as pale yellow solid. 1H NMR (300 MHz, MeOD) δ 8.78 (d, 1H), 8.34 (d, 1H), 8.20 (d, 1H), 7.72 (m, 2H), 7.63 (d, 1H), 7.35 (d, 1H), 7.30 (d, 1H), 7.20 (d, 1H), 5.07 (s, 2H), 2.95 (s, 1H), 2.34 (s, 3H), 1.55 (m, 5H), 1.05 (m, 5H); LC/MS m/z 437 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-947c8fc084d34f0f9581164f55b3fe12
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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