Dimethyl Sulfoxide → (S)-N-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide

HRID 1408205Notes

Reaction equation

HRID 1408205 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:13]([CH2:55][CH3:56])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:35])[C:22]2[CH:34]=[CH:33][CH:32]=[C:24]([C:25]([N:27]([CH2:29][CH2:30][OH:31])[CH3:28])=[O:26])[CH:23]=2)=[C:16]([C:36]2[CH:41]=[C:40]([C:42](=[O:54])[NH:43][C@@H:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH2:47][CH2:46][CH2:45]3)[CH:39]=[CH:38][N:37]=2)[CH:15]=1)[CH3:12]>C(Cl)Cl>[CH2:55]([N:13]([CH2:11][CH3:12])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:35])[C:22]2[CH:34]=[CH:33][CH:32]=[C:24]([C:25]([N:27]([CH3:28])[CH2:29][CH:30]=[O:31])=[O:26])[CH:23]=2)=[C:16]([C:36]2[CH:41]=[C:40]([C:42](=[O:54])[NH:43][C@@H:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH2:47][CH2:46][CH2:45]3)[CH:39]=[CH:38][N:37]=2)[CH:15]=1)[CH3:56]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 69631468(S)-N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-(2-hydroxyethyl)-N3-methylisophthalamide

Product 1

HCID 86705976(S)-N-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-methyl-N3-(2-oxoethyl)isophthalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of DMSO (4.8 mmol, 375 mg) in DCM (3 mL) at −78° C. was added a solution of oxalyl chloride (2.4 mmol, 305 mg) in DCM (0.4 mL). The mixture was stirred at −78° C. for 15 minutes. Then a solution of (S)—N1-(4-(diethylamino)-2-(4-((1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyridin-2-yl)phenyl)-N3-(2-hydroxyethyl)-N3-methylisophthalamide Example 194 (1.2 mmol, 742 mg) in DCM (1.7 mL) was added dropwise. The mixture was stirred at −78° C. for 3 h and quenched with triethylamine (0.85 mL). The mixture was stirred at −78° C. for 10 minutes, at 0° C. for 10 minutes, then diluted with water, and extracted with DCM (2×). The combined organic layers was washed with water (1×), dried, and concentrated. The residue was used without further purification.

Workup

  1. stirringThe mixture was stirred at −78° C. for 3 h
  2. customquenched with triethylamine (0.85 mL)
  3. stirringThe mixture was stirred at −78° C. for 10 minutes, at 0° C. for 10 minutes
  4. additiondiluted with water
  5. extractionextracted with DCM (2×)
  6. washThe combined organic layers was washed with water (1×)
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was used without further purification

Sources & evidence

ORD record
ord-ccfac8ded1ef4f0ba25737bc40cedf04
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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