Diisopropylethylamine → HCID 178452101, compound

HRID 1783810Notes

Reaction equation

HRID 1783810 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[ClH:15].N1C=CC([C:21]([NH2:23])=[NH:22])=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[ClH:15].[NH2:23][C:21]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[NH:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 178479321HCID 178479321, compound

Product 1

HCID 178452101HCID 178452101, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butyl 4-aminopiperidine-1-carboxylate (8.93 g, 44.6 mmol) and pyrazole carbox-amidine hydrochloride (6.536 g, 44.6 mmol) was added Hunig's base (7.77 ml, 44.6 mmol) and DMF (25 ml). The reaction was heated at 60° C. for 15 hours. The reaction was then cooled to room temperature and quenched by adding 400 ml of diethyl ether and stirring at room temperature for 2 hours. Product separated out as a white solid, which was filtered, washed and dried (10.9 g, 88%). M.p.=169-172° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.09 (d, J=8.8 HZ, 1H), 6.9-7.9 (br. s, 3H), 3.83 (d, J=13.6 Hz, 2H), 3.63 (m, 1H), 2.88 (m, 2H), 1.80 (m, 2H), 1.40 (s, 9H), 1.25 (m, 2H); LCMS: 243 [M+H]; calc. for C11H22N4O2.1.06HCl.0.2H2O: C, 46.39; H, 8.31; N, 19.68. Found C, 46.43; H, 8.31; N, 20.68.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customquenched
  3. additionby adding 400 ml of diethyl ether
  4. customProduct separated out as a white solid, which
  5. filtrationwas filtered
  6. washwashed
  7. customdried (10.9 g, 88%)

Sources & evidence

ORD record
ord-c53ef980bc6841fa899ade986d5382c8
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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