Borane → 5-tert-butyl-2-(4-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-ylamine

HRID 1661005Notes

Reaction equation

HRID 1661005 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[N:18](C=O)CCOC3)=[CH:9][CH:8]=2)[N:5]=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1.B.[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[C:21]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][N:18]3[CH2:26][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:11][CH:12]=2)[N:5]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 866258265-[4-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-morpholin-4-yl-methanone

Product 1

HCID 670216085-tert-butyl-2-(4-morpholin-4-ylmethyl-phenyl)-2H-pyrazol-3-ylamine

Procedure

To a solution of 490 mg 5-[4-(5-amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-morpholin-4-yl-methanone (1.49 mmol) in 13 mL THF, 3 mL (2.98 mmol) of borane (1M solution in THF) are added at rt. The reaction is stirred at rt for 12 h, concentrated, taken up in MeOH and concentrated again (3×). The residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH, gradient 0-5% MeOH) to give the title compound as a yellow solid. 1H-NMR (CDCl3): 7.50 (d, J=7.2 Hz, 2H), 7.40 (d, J=7.2 Hz, 2H), 5.52 (s, 1H), 3.73-3.70 (m, 5H), 3.51 (s, 2H), 2.47-2.44 (m, 3H), 1.32 (s, 9H).

Workup

  1. concentrationconcentrated
  2. concentrationconcentrated again (3×)
  3. customThe residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH, gradient 0-5% MeOH)

Sources & evidence

ORD record
ord-1c349c7e1b724585a26ca63fed5f5574
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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