Water → HCID 66696899, compound

HRID 1852545Notes

Reaction equation

HRID 1852545 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][CH:20]([CH:23]=O)[CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)(=O)C.ClCCCl>[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH2:19][CH2:18]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 59718926HCID 59718926, compound

Product 1

HCID 66696899HCID 66696899, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)-cyclohexanecarbaldehyde (39 mg), morpholine (14 μL) and acetic acid (2 drops) in DCE (2 mL) was stirred at RT for 2 hours; sodium triacetoxyborohydride was then added. The resulting mixture was stirred for 3 hours at RT. Water was added; the organic layer was separated and washed 3 times with water. The aqueous layer was re-extracted with DCM. The combined organic extracts were dried over Na2SO4 and filtered; the solvent was evaporated under reduced pressure and the residue was purified via preparative TLC to afford 13.2 mg of (4-benzotriazol-1-yl-pyrimidin-2-yl)-(4-morpholin-4-ylmethyl-cyclohexyl)-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.56 (1 H, d, J=8.31 Hz), 8.36-8.46 (1 H, bd), 8.12 (1 H, d, J=8.31 Hz), 7.55-7.69 (1 H, m), 7.40-7.52 (2H, m), 5.22-5.64 (1 H, m), 3.49-3.96 (5 H, m), 2.12-2.56 (6 H, m), 1.46-2.04 (5 H, m), 1.03-1.46 (4 H, m).

Workup

  1. stirringThe resulting mixture was stirred for 3 hours at RT
  2. customthe organic layer was separated
  3. washwashed 3 times with water
  4. extractionThe aqueous layer was re-extracted with DCM
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified via preparative TLC

Sources & evidence

ORD record
ord-5d8695afe55f4d3bbf63bee327b28139
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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