Hydrochloric Acid → HCID 58709868, compound

HRID 2375868Notes

Reaction equation

HRID 2375868 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:31][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26](=[O:29])[N:25]([CH3:30])[CH:24]=4)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCN(CC)CC.[C:40]([N:44]=[C:45]=[O:46])([CH3:43])([CH3:42])[CH3:41]>CO.CN(C=O)C>[C:40]([NH:44][C:45]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[NH:31][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:28]=[CH:27][C:26](=[O:29])[N:25]([CH3:30])[CH:24]=4)[C:16]=3[CH:15]=2)[CH2:12][CH2:13]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62412tert-Butyl isocyanate2×HCID 58709861HCID 58709861, compound

Product 1

HCID 58709868HCID 58709868, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

4-[4-(1-Methyl-6-oxo-1,6-dihydropyridin-3-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (38.0 mg, 0.0845 mmol), 9M of Hydrogen chloride in Methanol (2 mL) and Methanol (2 mL) were combined, and the above miture was stirred at rt for 3 h. The reaction mixture was concentrated in vacuo to obtain a black solid. DMF (3 mL), NEt3 (58.9 μL, 0.423 mmol) and tert-butyl isocyanate (14.5 μL, 0.127 mol) were added, and the mixture was stirred at rt under N2 for 1.5 h. Another portion of tert-butyl isocyanate was added and the reaction was stirred overnight. The mixture was concentrated in vacuo, and the residue was purified by HPLC to obtain the title compound as pink solid. 1H NMR (CD3OD, 400 MHz): δ=1.36 (s, 9H), 2.56 (brs, 2H), 3.61 (m, 2H), 3.62 (s, 3H), 4.07 (brs, 2H), 6.29 (brs, 1H), 6.58 (s, 1H), 6.60 (d, 1H, J=9.6 Hz), 7.71 (dd, 1H, J=2.8 & 9.6 Hz), 8.16 (brs, 2H), 8.19 (s, 1H), 8.25 (d, 1H, J=2.4 Hz). MS (ES+): m/z 422.12 (100) [MH+]. HPLC: tR=20.11 min (ZQ2000, polar—5 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto obtain a black solid
  3. stirringthe mixture was stirred at rt under N2 for 1.5 h
  4. stirringthe reaction was stirred overnight
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-69735f2ab0164650af8aaabcc6416f19
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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