Methanesulfonyl chloride → HCID 59639601, compound

HRID 2250087Notes

Reaction equation

HRID 2250087 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][CH2:29][NH2:30])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].C(N(C(C)C)CC)(C)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:27][CH2:28][CH2:29][NH:30][S:42]([CH3:41])(=[O:44])=[O:43])[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 596395772-[(2-Aminoethyl)amino]-8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 59639601HCID 59639601, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of Example 157 (250 mg, 0.58 mmol), di-isopropylethylamine (111 uL, 0.64 mmol) and CH2Cl2 (10 mL) was cooled to −5° and methanesulfonyl chloride (50 uL, 0.64 mmol) was added and the resulting soln was warmed to 23°, stirred 15 min, diluted with CH2Cl2 (75 mL) and washed with 10% aq NaOH (2×20 mL) and satd aq NaCl, dried (Na2SO4), and concentrated to afford a brown solid. Chromatotron chromatography (CH2Cl2/CH3OH) and crystallization from Et2O afforded a pink solid. mp=105-115° (dec); LC MS (m/e)=504.2 (MH+). Rt=1.94 min.

Workup

  1. temperaturethe resulting soln was warmed to 23°
  2. washwashed with 10% aq NaOH (2×20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford a brown solid
  6. customChromatotron chromatography (CH2Cl2/CH3OH) and crystallization from Et2O
  7. customafforded a pink solid

Sources & evidence

ORD record
ord-cddda9c14df5472dadd4093d9a6740c0
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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