Cyclopropanecarboxylic acid → HCID 24882766, compound

HRID 2421056Notes

Reaction equation

HRID 2421056 reaction equation
[N:1]1([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:6][CH2:5][CH:4]([N:7]2[C@@H:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]3[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[CH:23]1([C:26](O)=[O:27])[CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:23]1([C:26]([N:20]2[CH2:21][CH2:22][CH:17]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C@@H:11]5[CH2:12][CH2:13][CH2:14][CH2:15][C@H:10]5[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]3)[CH2:18][CH2:19]2)=[O:27])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59025410HCID 59025410, compound

Product 1

HCID 24882766HCID 24882766, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (3aR,7aR)-1-(1,4′-bipiperidin-4-yl)octahydro-2H-benzimidazol-2-one, 0.25 mmol) in dry DMF (3 mL) was added cyclopropanecarboxylic acid (26 mg, 0.3 mmol) followed by HATU (114 mg, 0.3 mmol) and diisopropylethylamine (0.10 mL, 0.5 mmol) and the mixture was stirred at room temperature for 1 h. The reaction was quenched with water (5 mL) and the solvent was removed in vacuo. Dichloromethane (15 mL) was added and washed with saturated NaHCO3 (10 mL) and brine (10 mL) and dried over Na2SO4. The crude product was purified with high pH prep-LCMS to provide the title compound (48 mg, 51%) as white powder. 1H NMR (400 MHz, METHANOL-D4): δ ppm 0.61-0.81 (m, 4H), 1.16-1.43 (m, 6H), 1.50-1.67 (m, 2H), 1.68-1.98 (m, 8H), 2.13-2.29 (m, 3H), 2.44-2.62 (m, 2H), 2.80-3.10 (m, 5H), 3.48-3.66 (m, 1H), 4.31 (d, J=13.28 Hz, 1H), 4.47 (d, J=13.28 Hz, 1H). MS (M+1): 375.2

Workup

  1. customThe reaction was quenched with water (5 mL)
  2. customthe solvent was removed in vacuo
  3. additionDichloromethane (15 mL) was added
  4. washwashed with saturated NaHCO3 (10 mL) and brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified with high pH prep-LCMS

Sources & evidence

ORD record
ord-22afd5909b3c449697c2b68014c4751c
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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