Butanedione → HCID 22036570, compound

HRID 1790173Notes

Reaction equation

HRID 1790173 reaction equation
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(=O)[C:20](C)=[O:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:38]1[CH2:42][O:41][CH2:40]C1>CC(OC)(C)C>[CH3:20][O:21][CH:42]([O:41][CH3:40])[CH2:38][NH:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([CH2:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[N:9]=[CH:10]2

Participants

6

Reactant 4

HCID 650ButanedioneHCID 8028Tetrahydrofuran2×HCID 5049666Sodium triacetoxyborohydride2×HCID 113107771-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-5-ylamine

Product 1

HCID 22036570HCID 22036570, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine (1.14 g, 0.497 mmol) in 62 mL of dry THF was added 2.04 mL of dimethyl glyoxal in MTBE (45% glyoxal by weight). A slurry of NaBH(OAc)3 (1.66 g, 7.83 mmol) in THF (10 mL) was slowly added via addition funnel over 60 minutes, and the mixture stirred at room temperature. After 12 hours, an additional equivalent of NaBH(OAc)3 was added. After an additional 12 hours, the mixture was quenched with saturated. NaHCO3, filtered, and the solvents removed under reduced pressure. The residue was purified via column chromatography eluting with 5–15% Et3N in EtOAc to provide 650 mg (2.04 mmol) of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.50–1.74 (m, 4 H) 2.33–2.46 (m, 4 H) 2.81 (t, J=6.78 Hz, 2 H) 3.14 (t, J=5.76 Hz, 2 H) 3.33 (t, 6 H) 4.38 (t, J=6.78 Hz, 2 H) 4.54 (t, J=5.42 Hz, 1 H) 5.26 (t, J=6.10 Hz, 1 H) 6.63–6.73 (m, J=2.03 Hz, 1 H) 6.91 (dd, J=8.98, 2.20 Hz, 1 H) 7.28–7.46 (m, J=8.81 Hz, 1 H) 7.64–7.78 (m, 1 H); MS (ESI) m/z 319 [M+H]+.

Workup

  1. waitAfter an additional 12 hours
  2. customthe mixture was quenched with saturated
  3. filtrationNaHCO3, filtered
  4. customthe solvents removed under reduced pressure
  5. customThe residue was purified via column chromatography
  6. washeluting with 5–15% Et3N in EtOAc

Sources & evidence

ORD record
ord-4aea544eff374c7797839e5e5d48937d
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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