Hydrochloric Acid → HCID 18697947, compound

HRID 2289487Notes

Reaction equation

HRID 2289487 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]4[CH:36]=[CH:35][C:30]5[N:31]=[C:32]([CH3:34])[NH:33][C:29]=5[CH:28]=4)[N:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>ClCCl.CO.C(OCC)C>[CH3:34][C:32]1[NH:33][C:29]2[CH:28]=[C:27]([NH:26][C:22]3[N:21]=[C:20]([C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)=[N:15][CH:16]=4)[CH:25]=[CH:24][N:23]=3)[CH:36]=[CH:35][C:30]=2[N:31]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 18697955HCID 18697955, compound

Product 1

HCID 18697947HCID 18697947, compoundYield 35.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-(4-tert-butoxycarbonylpiperazin-1-yl)pyrid-5-yl)-N-(2-methylbenzimidazol-5-yl)-2-pyrimidineamine (70 mg, 0.14 mmol) in a mixture of dichloromethane (5 ml) and methanol (3 ml) was treated with hydrogen chloride (5 ml of a 1M solution in diethyl ether, 5.00 mmol) then stirred for 18 h at room temperature. The precipitate which formed was collected by filtration then subjected to column chromatography (silica, 0.88 ammonia solution-methanol-dichloromethane, 1:5:94) to afford the title compound (19 mg) as a yellow solid m.p. 245-250°. δH (d6DMSO) 2.45 (3H, s), 2.80 (4H, m), 3.38 (4H,m), 6.91 (1H, d, J 9.0 Hz), 7.24 (1H, d J 5.2 Hz), 7.35 (2H, s), 8.11 (1H, s), 8.25 (1H, m), 8.39 (1H, d, J 5.2 Hz), 8.93 (1H, d, J 2.2 Hz), 9.41 (1H, br s) and 11.50 (1H, br s).

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3002ef72d109491caf1625c1e63e247e
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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