Dimethylcarbamoyl Chloride → HCID 22730503, compound

HRID 2356064Notes

Reaction equation

HRID 2356064 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) δ 1.93 (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-b02cf46d2bf04bfc8af972b368bc9ef2
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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