(1,1-Dimethylethyl)urea → HCID 71254160, compound

HRID 1775102Notes

Reaction equation

HRID 1775102 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][CH2:20][C@H:19]([NH:23]C(=O)OC(C)(C)C)[CH2:18]4)[CH:14]=[CH:13][CH:12]=3)=[N:9][N:8](C3CCCCO3)[C:5]2=[CH:6][N:7]=1.CC([NH:41][C:42]([NH2:44])=[O:43])(C)C>>[NH2:23][C@H:19]1[CH2:20][CH2:21][CH2:22][N:17]([C:15]2[N:16]=[C:11]([C:10]3[C:4]4[C:5](=[CH:6][N:7]=[C:2]([NH:41][C:42]([NH2:44])=[O:43])[CH:3]=4)[NH:8][N:9]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:18]1

Participants

3

Reactant 2

HCID 14233(1,1-Dimethylethyl)ureaHCID 86676698HCID 86676698, compound

Product 1

HCID 71254160HCID 71254160, compoundYield 23%

Procedure

Following the Buchwald-Hartwig procedure of Example 224, tert-butyl (3S)-1-(6-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ylcarbamate and (1,1-dimethylethyl)urea were reacted and deprotected by the procedure of Example 229. The mixture was purified via reverse phase HPLC using a gradient of MeOH in water with 0.1% NH4OH to afford 20 mg (23%) of 298 over three steps. ESI MS m/z 353.2 (M+1). 1H NMR (400 MHz, DMSO): 9.14 (s, 1H), 8.96 (s, 1H), 8.75 (s, 1H), 8.40 (s, 2H), 7.63 (t, J=8.0 Hz, 1H), 7.45 (d, J=7.4 Hz, 1H), 6.80 (d, J=8.5 Hz, 1H), 6.48 (s, 2H), 4.92 (d, J=11.4 Hz, 1H), 4.05 (d, J=12.9 Hz, 1H), 3.09 (m, 1H), 2.94-2.77 (m, 2H), 2.54 (s, 2H), 2.05 (d, J=9.7 Hz, 1H), 1.84 (d, J=13.1, Hz, 1H), 1.64-1.42 (m, 2H)

Workup

  1. customwere reacted
  2. customThe mixture was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-30672072971c4d1e8fc2b7386920ea30
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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