Hydrochloric Acid → HCID 67316367, compound

HRID 1014427Notes

Reaction equation

HRID 1014427 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24](N)=[O:25])[C:5]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:6]=2[N:7]=1.[NH2:31][C:32]1[CH:33]=[C:34]([NH:39][C:40](=[O:45])[CH2:41][N:42]([CH3:44])[CH3:43])[CH:35]=[CH:36][C:37]=1[CH3:38].[I-].[K+].Cl.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:43][N:42]([CH3:44])[CH2:41][C:40]([NH:39][C:34]1[CH:35]=[CH:36][C:37]([CH3:38])=[C:32]([NH:31][C:2]2[N:3]3[C:4](=[N:21][C:22]4[C:23]([C:24]3=[O:25])=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:5]3[CH:10]=[CH:9][N:8]([S:11]([C:14]4[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=4)(=[O:12])=[O:13])[C:6]=3[N:7]=2)[CH:33]=1)=[O:45]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 17607975N-(3-Amino-4-methylphenyl)-N~2~,N~2~-dimethylglycinamideHCID 25150094HCID 25150094, compound

Product 1

HCID 67316367HCID 67316367, compoundYield 823.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a pressurized vessel was added 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (1.0 g, 2.27 mmol), N1-(3-amino-4-methylphenyl)-N2,N2-dimethylglycinamide (0.590 g, 2.83 mmol), potassium iodide (<10 mg) and hydrochloric acid as a 4.0M solution in dioxanes (ca 4 mL). The resulting suspension was stirred until all solids had completely dissolved (24 hr.) The reaction was poured into into saturated sodium bicarbonate and diluted with dichloromethane. The organic layer was dried over sodium sulfate, volatiles removed under reduced pressure, and the solids triturated with diethyl ether to afford N2,N2-dimethyl-N1-[4-methyl-3-({3-[(4-methylphenyl)sulfonyl]-7-oxo-3,7-dihydropyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-5-yl}amino)phenyl]glycinamide (1.11 g, 18.7 mmol, 82% yield) of sufficient purity for use in subsequent transformations. ESIMS (M+H)=596.

Workup

  1. dissolutionhad completely dissolved (24 hr.) The reaction
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customvolatiles removed under reduced pressure
  4. customthe solids triturated with diethyl ether

Sources & evidence

ORD record
ord-d54ebd19625045e58ed574fbbbb7f8e3
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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