Ammonia → HCID 68542776, compound

HRID 1441448Notes

Reaction equation

HRID 1441448 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C@H:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][N:29]=[CH:28]3)O1.N.[C:36]([C:40]([OH:42])=[O:41])([F:39])([F:38])[F:37]>>[F:37][C:36]([F:39])([F:38])[C:40]([OH:42])=[O:41].[NH:30]1[C:31]2[C:27](=[CH:26][C:25]([C:2]3[N:7]=[N:6][C:5]([O:8][C@H:9]4[CH:14]5[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]5)[CH2:10]4)=[CH:4][CH:3]=3)=[CH:33][CH:32]=2)[CH:28]=[N:29]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 86598854HCID 86598854, compound

Product 1

HCID 68542776HCID 68542776, compound

Procedure

The product of Example 30A (132 mg, 0.549 mmol) was the product of Example 49A (325 mg, 1.33 mmol) according to the procedure of Example 26B. The title product was purified by preparative HPLC (column: Xterra™, RP-18, 5 μm, 30×100 mm; eluting solvent, MeCN/H2O (with 0.1% v. TFA), (v. 90/10 to 10/90 over 20 min.); flow rate, 40 mL/min.; uv, 254 nm) to provide a solid (115.3 mg, yield, 45.8%). 1H NMR (300 MHz, CD3OD) δ 1.92-2.25 (m, 3H) 2.34-2.49 (m, 1H) 2.63-2.72 (m, 1H) 3.34-3.57 (m, 5H) 3.99 (dd, J=13.90, 8.14 Hz, 1H) 5.54-5.61 (m, 1H) 7.36 (d, J=9.49 Hz, 1H) 7.69 (d, J=8.82 Hz, 1H) 8.08 (dd, J=8.82, 1.70 Hz, 1H) 8.16-8.23 (m, 2H) 8.38 (dd, J=1.53, 0.85 Hz, 1H) ppm. MS (DCI/NH3) m/z 322 (M+H)+. Anal. Calculated for C18H19N5O.1.2 CF3CO2H: C, 53.47; H, 4.44; N, 15.28. Found: C, 53.67; H, 3.99; N, 15.40.

Workup

  1. customThe title product was purified by preparative HPLC (column: Xterra™, RP-18, 5 μm, 30×100 mm; eluting solvent, MeCN/H2O (with 0.1% v. TFA), (v. 90/10 to 10/90 over 20 min.); flow rate, 40 mL/min.; uv, 254 nm)
  2. customto provide
  3. customa solid (115.3 mg, yield, 45.8%)

Sources & evidence

ORD record
ord-1b6072e341ea4dca961f34d06458bb68
Source dataset
uspto-grants-2010_02
Patent number
US07655657B2

Reaction notes

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