2-(Dimethylamino)ethanol → HCID 66604403, compound

HRID 2410727Notes

Reaction equation

HRID 2410727 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C:33]1[CH:34]=[CH:35][C:36]2[C:37]3[N:45]=[C:44]([C:46]4[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=4)[CH:43]=[C:42]([C:54]([NH2:56])=[O:55])[C:38]=3[NH:39][C:40]=2[CH:41]=1.[CH3:57][N:58]([CH3:62])[CH2:59][CH2:60]O>C1COCC1>[CH3:57][N:58]([CH3:62])[CH2:59][CH2:60][O:32][C:33]1[CH:34]=[CH:35][C:36]2[C:37]3[N:45]=[C:44]([C:46]4[CH:47]=[CH:48][C:49]([O:52][CH3:53])=[CH:50][CH:51]=4)[CH:43]=[C:42]([C:54]([NH2:56])=[O:55])[C:38]=3[NH:39][C:40]=2[CH:41]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178488616HCID 178488616, compound

Product 1

HCID 66604403HCID 66604403, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethyl azodicarboxylate (0.057 mL, 0.360 mmol) was added to an ice-cooled solution of triphenylphosphine (94 mg, 0.360 mmol) in dry THF (1 mL). The bath was removed and a solution of 7-hydroxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (Example 207, 60 mg, 0.180 mmol) and 2-(dimethylamino)ethanol (24 mg, 0.270 mmol) in dry THF (1 mL) was added after 15 minutes. After stirring for 2 hr at room temperature, the reaction was quenched with brine and extracted with EtOAc. The extracts were dried with sodium sulfate and the solvent was removed. Radial silica gel chromatography of the residue (step gradient elution with methylene chloride containing 10 to 60% methanol) followed by SCX cartridge purification gave 7-(2-(dimethylamino)ethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (12 mg) as a yellow glass. MS (ESI) m/z 405.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.34 (1H, br. s.), 8.56 (1H, s), 8.28 (1H, s), 8.23 (2H, d, J=8.85 Hz), 8.10 (1H, d, J=8.55 Hz), 7.83 (1H, s), 7.28 (1H, d, J=2.14 Hz), 7.10 (2H, d, J=8.85 Hz), 6.89 (1H, dd, J=8.55, 2.44 Hz), 4.15 (2H, t, J=5.95 Hz), 3.85 (3H, s), 2.70 (2H, t, J=5.80 Hz), 2.27 (6H, s).

Workup

  1. customThe bath was removed
  2. customthe reaction was quenched with brine
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried with sodium sulfate
  5. customthe solvent was removed
  6. washRadial silica gel chromatography of the residue (step gradient elution with methylene chloride containing 10 to 60% methanol)
  7. customfollowed by SCX cartridge purification

Sources & evidence

ORD record
ord-8c75aec3ed9841a7a39bdaf82e674cc5
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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