Chloroacetyl chloride → HCID 86698289, compound

HRID 2408970Notes

Reaction equation

HRID 2408970 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[Se:15][C:14]=1[C:22]([NH2:24])=[O:23].[Cl:25][CH2:26][C:27](Cl)=[O:28]>C1COCC1>[Cl:25][CH2:26][C:27]([NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:19])[CH3:20])[Se:15][C:14]=1[C:22]([NH2:24])=[O:23])=[O:28]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 86698290HCID 86698290, compound

Product 1

HCID 86698289HCID 86698289, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(6-aminoquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide (510 mg, 1.31 mmol) in THF (10 mL) was added a solution of chloroacetyl chloride (0.105 mL, 1.31 mmol) in THF (1.0 mL) at rt. The mixture was stirred at rt for 30 min (solid separated). The solution was poured into ice cold water and stirred for 15 min. The separated solid was filtered, washed with water and dried to give the product as a yellow color solid (540 mg, 80%). This crude product was further chromatographed and recrystallized from chloroform-methanol. Mp 262-264° C.; IR (KBr) vmax 3437, 3109, 2961, 1706, 1652, 1608, 1575, 1541, 1464, 1386, 1355, 1311, 1241, 1137, 1086, 858, 834, 790 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 12.79 (1H, s, exchangeable with D2O), 10.83 (1H, s, exchangeable with D2O), 8.83 (1H, s), 8.73 (1H, s), 8.60 (1H, br s), 8.01-8.03 (1H, m), 7.89 (1H, d, J=8.8 Hz), 7.68 (2H, br s), 4.41 (2H, s), 1.47 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 167.9, 167.2, 164.9, 154.9, 153.2, 146.3, 145.5, 137.2, 128.7, 126.7, 121.1, 115.2, 113.1, 110.0, 43.3, 36.5, 32.2; LC-MS (negative ion mode): m/z 462, 464, 466 (M−H)−.

Workup

  1. custom(solid separated)
  2. additionThe solution was poured into ice cold water
  3. stirringstirred for 15 min
  4. filtrationThe separated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5102112aca3d4b68a803b7256092a43a
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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