Dimethylcarbamoyl Chloride → HCID 71466170, compound

HRID 572669Notes

Reaction equation

HRID 572669 reaction equation
Cl.[F:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[CH2:21][CH:20]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[O:19][N:18]=3)[N:14]=[C:13]([CH3:28])[N:12]=2)=[O:10])=[CH:5][C:4]=1[O:31][CH3:32].[CH3:33][N:34]([CH3:38])[C:35](Cl)=[O:36]>C(Cl)Cl>[CH3:33][N:34]([CH3:38])[C:35]([N:25]1[CH2:24][CH2:23][CH:22]([CH:20]2[O:19][N:18]=[C:17]([C:15]3[N:14]=[C:13]([CH3:28])[N:12]=[C:11]([C:9]([NH:8][CH2:7][C:6]4[CH:29]=[CH:30][C:3]([F:2])=[C:4]([O:31][CH3:32])[CH:5]=4)=[O:10])[CH:16]=3)[CH2:21]2)[CH2:27][CH2:26]1)=[O:36]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 71466164HCID 71466164, compound

Product 1

HCID 71466170HCID 71466170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide hydrochloride (0.12 g, 0.25 mmol, Preparation #K.1) and TEA (0.091 g, 0.9 mmol, Sd Fine Chem) in DCM (15 mL) was added dimethyl carbamoyl chloride (0.033 g, 0.31 mmol, Aldrich). The reaction mixture was slowly warmed to RT and stirred for about 1 h. The reaction mixture was diluted with DCM (20 mL) and washed with water (2×15 mL). The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. The crude material obtained was purified using silica gel column chromatography eluted with 2-3% methanol in DCM. Relevant fractions containing the required compound were combined and evaporated to dryness under reduced pressure to afford 6-(5-(1-(dimethylcarbamoyl)piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)-N-(4-fluoro-3-methoxybenzyl)-2-methylpyrimidine-4-carboxamide as an off white solid 0.064 g (50%): LC/MS (Table 1, Method c) Rt=1.83 min; MS m/z: 499.3 (M+H)+.

Workup

  1. washwashed with water (2×15 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material obtained
  5. customwas purified
  6. washeluted with 2-3% methanol in DCM
  7. additionRelevant fractions containing the required compound
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bccb3c1423b4434a93dad6aa847bfcf5
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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