Dimethylformamide → HCID 59656423, compound

HRID 2054889Notes

Reaction equation

HRID 2054889 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 □L, 0.38 mmol) and triethylamine (88 □L, 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-0d1b0766513e42c1a2be3e5ee0bb2970
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Reaction notes

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