Hydrochloric Acid → HCID 86637347, compound

HRID 2189319Notes

Reaction equation

HRID 2189319 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:18]=[CH:19][C:20]4[CH:25]=[C:24]([CH:26]=O)[N:23]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:21]=4[N:22]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.[O:34]([NH2:36])[CH3:35].Cl.[CH3:38]CO>>[CH2:31]([CH:28]([N:23]1[C:21]2[N:22]=[C:17]([NH:16][C:13]3[CH:12]=[CH:11][C:10]([N:7]4[CH2:6][CH2:5][N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8]4)=[CH:15][CH:14]=3)[N:18]=[CH:19][C:20]=2[CH:25]=[C:24]1[C:26](=[N:36][O:34][CH3:35])[CH3:38])[CH2:29][CH3:30])[CH3:32]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 23624284HCID 23624284, compound

Product 1

HCID 86637347HCID 86637347, compound

Procedure

A mixture of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (25 mg, 0.057 mmol), methoxylamine hydrochloride (20 mg, 0.22 mmol) and 6N HCl (0.03 mL) in EtOH (1 mL) is stirred at ambient temperature for 6 h. The mixture was quenched with saturated NaHCO3 aqueous solution, extracted with CH2Cl2. The extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give the crude product. The crude product is purified by preparative HPLC to give 12 mg of 1-{4-[4-(7-(1-ethyl-propyl)-6-{1-methoxyimino-ethyl}-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-phenyl]-piperazin-1-yl}-ethanone as a bright yellow solid.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 aqueous solution
  2. extractionextracted with CH2Cl2
  3. washThe extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-176745a0bae246109d192cf5aca26a41
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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