1-Butanesulfonyl chloride → HCID 68253359, compound

HRID 2092598Notes

Reaction equation

HRID 2092598 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:32])=[C:6]([N:8]2[CH2:31][CH2:30][C:11]3[N:12]=[C:13]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([N:23]5[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]5)=[CH:19][CH:18]=4)[N:14]=[CH:15][C:10]=3[CH2:9]2)[CH:7]=1.[CH2:33]([S:37](Cl)(=[O:39])=[O:38])[CH2:34][CH2:35][CH3:36]>N1C=CC=CC=1>[CH3:32][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:37]([CH2:33][CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])=[CH:7][C:6]=1[N:8]1[CH2:31][CH2:30][C:11]2[N:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]4)=[CH:19][CH:18]=3)[N:14]=[CH:15][C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 754301-Butanesulfonyl chlorideHCID 67329109HCID 67329109, compound

Product 1

HCID 68253359HCID 68253359, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution [6-(5-Amino-2-methyl-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (50.0 mg, 0.116 mmol) in Pyridine (1 ml) at 0° C. was added Butane-1-sulfonyl chloride (21.3 mg, 0.139 mmol) dropwise The reaction mixture was stirred for 15 minutes at 0° C. and then allowed to attain room temperature. It was then further stirred for 3 hours at room temperature. The reaction mixture was concentrated under vacuum. The reaction mass was then, diluted with water and extracted with dichloromethane. The dichloromethane layer was washed with water, then with brine solution. The organic layer is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (SiO2, 2-10% methanol in chloroform) to give 50.4 mg (78.9%) Butane-1-sulfonic acid (4-methyl-3-{2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-phenyl)-amide [49] as off white solid.

Workup

  1. customto attain room temperature
  2. stirringIt was then further stirred for 3 hours at room temperature
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additiondiluted with water
  5. extractionextracted with dichloromethane
  6. washThe dichloromethane layer was washed with water
  7. dry with materialThe organic layer is dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product obtained
  10. customwas purified by column chromatography (SiO2, 2-10% methanol in chloroform)

Sources & evidence

ORD record
ord-f4c0a9fc4537437d83beb22e1e3d207c
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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