Hydrochloric Acid → HCID 178423297, compound

HRID 1371158Notes

Reaction equation

HRID 1371158 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:21]=[CH:20][N:19]([S:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)(=[O:24])=[O:23])[CH:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1.CCOC(C)=O.[ClH:37]>CO>[OH2:23].[ClH:37].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[CH:21]=[CH:20][N:19]([S:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)(=[O:24])=[O:23])[CH:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423296HCID 178423296, compound

Product 1

HCID 178423297HCID 178423297, compoundYield 162.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 1-(phenylsulfonyl)-3-(1-pyrrolidinylvinyl)pyrrole (freshly prepared before use) (0.97 g, 4.68 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.41 g, 4.68 mmol), N,N-diisopropyl ethyl amine (Aldrich Chemical Company) (0.8 mL, 4.68 mmol), piperidine (Aldrich Chemical Company) (0.7 mL, 7.5 mmol), NEt3 (Aldrich Chemical Company) (1.0 mL) and SnCl2 (Aldrich Chemical Company) (14 mL of a 2M solution in DMF). The residue was purified by flash chromatography on silica gel with 95:5 CHCl3:MeOH as elutant to give 186 mg (9%) of the free base as a tan colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.64 (br s, 6), 2.38 (s, 3), 3.68 (br s, 4), 6.60 (s, 1), 6.92 (s, 1), 7.477 (s, 1), 7.68 (t, 2, J=7.5), 7.77 (t, 1, J=7.5), 8.00 (d, 2, J=7.6), 8.09 (br s, 1), 10.74 (s, 1). MS m/z: 422 (M+1). To a hot solution of 3-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)-1-(phenylsulfonyl)pyrrole (0.18 g, 0.43 mmol) in 5:1 EtOAc:MeOH (40 mL) was added 1N etheral HCl (Aldrich Chemical Company) (432 mL, 0.43 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (2×5 mL) and dried under vacuum to give 166 mg (85%) of the title compound as a brown colored powder. Mp: 183-185.5° C. 1H NMR (DMSO-d6; 500 MHz): δ 1.67 -1.69 (m, 6), 2.54 (s, 3), 4.02 (s, 4), 6.79 (s, 1), 7.06 (s, 1), 7.56 (t, 1, J=2.7), 7.69 (t, 2, J=7.8), 7.79 (t, 1, J=7.6), 8.04 (d, 2, J=8.0), 8.31 (s, 1), 11.70 (s, 1), 14.14 (s, 1). MS m/z: 422 (M+1) Anal. Calcd for C22H23N5O2S.HCl.1.5H2O: C, 54.26; H, 5.63; N, 14.39; Cl, 7.28. Found C, 54.31; H, 5.39; N, 13.99; Cl, 7.58.

Workup

  1. customCrystallization
  2. temperaturecooled
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with Et2O (2×5 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-500d581643c1404ab03067bf530c6bd6
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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