Water → (S)-1-(7-bromo-3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(2-methoxy-1-phenylethyl)urea

HRID 588212Notes

Reaction equation

HRID 588212 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([O:24][CH3:25])=[N:22][NH:23][C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1C(=O)N([Br:33])C(=O)C1.O>CN(C=O)C>[Br:33][C:16]1[C:17]2[NH:23][N:22]=[C:21]([O:24][CH3:25])[C:18]=2[CH:19]=[N:20][C:15]=1[NH:14][C:12]([NH:11][C@@H:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][O:2][CH3:1])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 118271892(S)-1-(2-methoxy-1-phenylethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Product 1

HCID 118271804(S)-1-(7-bromo-3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(2-methoxy-1-phenylethyl)urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1-(2-Methoxy-1-phenylethyl)-3-(3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (Example 41, 53 mg, 0.155 mmol) and NBS (35.5 mg, 0.199 mmol) were stirred in DMF (1 mL) at room temperature for 6 hours. Water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by MPLC (12-100% EtOAc-hexanes) gave (S)-1-(7-bromo-3-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(2-methoxy-1-phenylethyl)urea MS: [M+H]+ m/z 420. 1H NMR (500 MHz, DMSO-d6) δ 12.67 (s, 1H), 9.08 (d, J=7.0 Hz, 1H), 8.67 (s, 1H), 7.98 (s, 1H), 7.35-7.30 (m, 4H), 7.25-7.21 (m, 1H), 5.03-4.98 (m, 1H), 4.01 (s, 3H), 3.63-3.56 (m, 2H), 3.27 (s, 3H).

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by MPLC (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-6379a0f8241b45b8a9d6ec30ac3517ce
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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