Dimethylcarbamoyl Chloride → HCID 22730503, compound

HRID 2085732Notes

Reaction equation

HRID 2085732 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:5][C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][CH2:37][CH2:38][S:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:32]([N+:46]([O-:48])=[O:47])[CH:31]=2)(=[O:29])=[O:28])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C.[CH3:56][N:57]([CH3:61])[C:58](Cl)=[O:59]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][N:15]([C:58]([N:57]([CH3:61])[CH3:56])=[O:59])[CH2:16][CH2:17]2)[CH:6]=[CH:5][C:4]=1[C:18]1[CH:19]=[CH:20][C:21]([C:24]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][CH2:37][CH2:38][S:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[C:32]([N+:46]([O-:48])=[O:47])[CH:31]=2)(=[O:28])=[O:29])=[O:25])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 22730650HCID 22730650, compound

Product 1

HCID 22730503HCID 22730503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 183D (108 mg, 0.157 mmol) and triethylamine (45 μL, 0.32 mmol) in THF (2 mL) at room temperature was treated with dimethylcarbamic chloride (14 uL, 0.157 mmol), and stirred for 30 minutes. The mixture was purified by flash column chromatography on silica gel with 10:10:80 methanol/acetonitrile/ethyl acetate to provide the desired product. MS (ESI(−)) m/e 759 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ1.93 (m, 2H), 2.65 (t, 2H), 2.74 (s, 6H), 2.89 (m, 2H), 3.08 (m, 4H), 3.34 (m, 6H), 3.61 (m, 2H), 3.75 (s, 3H), 6.88 (d, 1H), 6.96 (s, 1H), 7.01 (d, 1H), 7.21 (m, 2H), 7.30 (t, 2H), 7.41 (m, 3H), 7.88 (d, 1H), 7.89 (d, 2H), 8.51 (d, 1H), 8.54 (t, 1H).

Workup

  1. customThe mixture was purified by flash column chromatography on silica gel with 10:10:80 methanol/acetonitrile/ethyl acetate

Sources & evidence

ORD record
ord-17128ca1eb84418da27f883847bdd6b5
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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