3-(Dimethylamino)propanoyl chloride → 3-(dimethylamino)-N-(5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-yl)propanamide

HRID 1642585Notes

Reaction equation

HRID 1642585 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[C:19]([NH2:21])[C:18]([O:22][CH3:23])=[C:17]3[C:13]=2[C:14]2[CH:27]=[C:26]([CH3:28])[CH:25]=[N:24][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[CH3:29][N:30]([CH3:36])[CH2:31][CH2:32][C:33](Cl)=[O:34]>N1C=CC=CC=1>[CH3:29][N:30]([CH3:36])[CH2:31][CH2:32][C:33]([NH:21][C:19]1[C:18]([O:22][CH3:23])=[C:17]2[C:13]([C:14]3[CH:27]=[C:26]([CH3:28])[CH:25]=[N:24][C:15]=3[NH:16]2)=[C:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:7]=2)[CH:20]=1)=[O:34]

Participants

4

Reactant 2

HCID 141501833-(Dimethylamino)propanoyl chlorideHCID 588800795-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-amine

Product 1

HCID 588801173-(dimethylamino)-N-(5-(3-(ethylsulfonyl)phenyl)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-7-yl)propanamideYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of Compound 239 (150 mg, 0.38 mmol) in pyridine (2.0 mL) was added 3-(dimethylamino)propanoyl chloride (71 mg, 0.38 mmol) and the reaction mixture was heated at 105° C. for 5 h. and quenched with aqueous NH4Cl solution. Organic matter was extracted with CH2Cl2 (with 10% EtOH) and washed with brine. The organic extracts were dried (Na2SO4) and concentrated and purified by preparative HPLC to yield the title compound (103 mg, 55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.33 Hz, 3 H) 2.24 (s, 3 H) 2.33 (s, 6 H) 2.56 (t, J=5.81 Hz, 2 H) 2.62 (t, J=5.31 Hz, 2 H) 3.41 (d, J=7.33 Hz, 2 H) 3.93 (s, 3 H) 7.41 (d, J=1.26 Hz, 1 H) 7.87 (t, J=7.71 Hz, 1 H) 7.93-7.97 (m, 1 H) 8.03 (d, J=8.84 Hz, 1 H) 8.06 (s, 2 H) 8.22 (d, J=2.02 Hz, 1 H) 10.99 (br. s., 1 H) 12.07 (s, 1 H); [M+H] calc'd for C26H31N4O—4S, 495.2; found, 495.4.

Workup

  1. customquenched with aqueous NH4Cl solution
  2. extractionOrganic matter was extracted with CH2Cl2 (with 10% EtOH)
  3. washwashed with brine
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-031d882687c640d0bcf97d208c2e10c9
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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