Triethylamine → HCID 16666099, compound

HRID 219682Notes

Reaction equation

HRID 219682 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][CH:28]=1)[CH2:10][NH:11][C:12]([C:14]1[CH:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][CH:19]=1)=[O:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][CH:28]=1)[CH2:10][NH:11][C:12]([C:14]1[CH:19]=[N:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:16][CH:15]=1)=[O:13])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59805832HCID 59805832, compound

Product 1

HCID 16666099HCID 16666099, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.553 mmol) is added to a stirred solution of 2-phenyl-pyrimidine-5-carboxylic acid 3-amino-benzylamide (Example 115, 0.526 mmol) and triethylamine (1.05 mmol) in DCM (20 mL) at 0° C. The mixture is stirred at room temperature for an hour. The reaction mixture is quenched with 5% HCl and extracted with DCM (20 mL). The organic layer is separated, washed with water (20 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 0-5% MeOH in DCM to afford 2-(phenyl)-pyrimidine-5-carboxylic acid 3-methanesulfonylamino-benzylamide (200 mg) as a solid. MS: 383 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.41 (s, 3H), 4.76-4.72 (m, 2H), 7.00 (bs, N—H), 7.05-7.23 (m, 2H), 7.27-7.60 (m, 5H), 8.40-8.53 (m, 2H), 9.16 (s, 2H).

Workup

  1. customThe reaction mixture is quenched with 5% HCl
  2. extractionextracted with DCM (20 mL)
  3. customThe organic layer is separated
  4. washwashed with water (20 mL) and brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. washeluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-a6f98e57ea5a42dbade9995846e4514d
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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