Triethylamine → HCID 22676733, compound

HRID 1006269Notes

Reaction equation

HRID 1006269 reaction equation
C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=1)[C:28]([C:42]([O:44][CH2:45]C)=[O:43])=[C:27]2[C:47]1[CH:52]=[CH:51][C:50]([C:53]([CH3:56])([CH3:55])[CH3:54])=[CH:49][CH:48]=1>ClCCl>[C:53]([C:50]1[CH:49]=[CH:48][C:47]([C:27]2[C:26]3[C:30](=[CH:31][CH:32]=[C:24]([NH:23][C:20]([CH:17]4[CH2:19][CH2:18]4)=[O:21])[CH:25]=3)[N:29]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=3)[C:28]=2[C:42]([O:44][CH3:45])=[O:43])=[CH:52][CH:51]=1)([CH3:56])([CH3:54])[CH3:55]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 22676732HCID 22676732, compound

Product 1

HCID 22676733HCID 22676733, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.12 mL, 91 mg, 0.90 mmol), dimethylaminopyridine (20 mg, 0.16 mmol), and cyclopropanecarbonyl chloride (82 μL, 94 mg, 0.90 mmol) were added successively to a cooled (0° C.) and stirred solution of methyl 5-amino-3-(4-tert-butylphenyl)-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 160, 140 mg, 0.31 mmol) in dichloromethane (10 mL). The reaction was warmed to rt and stirred for 16 h. The solution was diluted with dichloromethane (50 mL), washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Flash chromatography of the residue over silica gel using 4:1 hexane/ethyl acetate afforded 58 mg (37%) of desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 9.38 (s, 1 H), 8.02 (d, 1 H), 7.37-7.65 (m, 6 H), 7.19 (dd, 1 H), 6.80 (dd, 1 H), 6.6-6.74 (m, 2 H), 5.81 (s, 2 H), 3.73 (s, 3 H), 3.62 (s, 3 H), 1.70-1.80 (m, 1 H), 1.40 (s, 9 H), 0.82-0.90 (m,2H),0.70-0.78 (m,2H).

Workup

  1. temperatureThe reaction was warmed to rt
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c8b1e45ac944002982c0d39077967ec
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…