Triethylamine → 2-{4-[4-(Vinylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

HRID 1441313Notes

Reaction equation

HRID 1441313 reaction equation
[N:1]1([C:7]2[CH:28]=[CH:27][C:10]([NH:11][C:12]3[N:17]=[C:16]([C:18]4[N:22]([CH:23]([CH3:25])[CH3:24])[C:21]([CH3:26])=[N:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[CH2:37][CH2:38][S:39](Cl)(=[O:41])=[O:40].CO.C(Cl)Cl>C(Cl)Cl>[CH:38]([S:39]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:28]=[CH:27][C:10]([NH:11][C:12]3[N:17]=[C:16]([C:18]4[N:22]([CH:23]([CH3:25])[CH3:24])[C:21]([CH3:26])=[N:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:9][CH:8]=2)[CH2:2][CH2:3]1)(=[O:41])=[O:40])=[CH2:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 21226129Dichloromethane methanolHCID 686857662-[4-(Piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Product 1

HCID 686838262-{4-[4-(Vinylsulphonyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-[4-(Piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (Example 20; 370 mg 0.98 mmol) was stirred in DCM (10 ml) at room temperature. Triethylamine (150 mg 1.49 mmol) was added followed by dropwise addition of 2-chloro-1-ethanesulphonyl chloride (196 mg 1.2 mmol) in DCM (1 ml). After stirring for 1.25 hours, the reaction was evaporated under reduced pressure and triturated with ether. The resulting solid was treated with water (15 ml), the basified with saturated sodium hydrogen carbonate solution and extracted into DCM (2×20 ml). The organics were washed with brine (10 ml), dried and evaporated to give a gum. After chromatography on silica gel using MeOH:DCM (3:97 to 5:95), the title compound was obtained as a yellow solid (140 mg 30.4%). NMR 1.39 (d, 6H), 2.46 (s, 3H), 3.16 (s, 8H), 5.68 (septuplet, 1H), 6.20 (d, 1H), 6.85 (dd, 1H), 6.91 (d, 2H), 6.95 (d, 1H), 7.38 (s, 1H), 7.47 (d, 2H), 8.30 (d, 1H), 9.16 (s, 1H); m/z 468.

Workup

  1. customthe reaction was evaporated under reduced pressure
  2. customtriturated with ether
  3. additionThe resulting solid was treated with water (15 ml)
  4. extractionextracted into DCM (2×20 ml)
  5. washThe organics were washed with brine (10 ml)
  6. customdried
  7. customevaporated
  8. customto give a gum

Sources & evidence

ORD record
ord-a13e5f0866324d92a58e033e2bdb2bec
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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