4-(Aminomethyl)piperidine → HCID 25123681, compound

HRID 2279992Notes

Reaction equation

HRID 2279992 reaction equation
[CH:1]1([N:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=4)=[N:18][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:30][N:31]([CH:35]([CH3:37])C)[CH:32]([CH3:34])C.[CH3:38][N:39](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NCC1CCNCC1>C(Cl)Cl>[CH:1]1([N:6]2[CH2:12][CH2:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]3[CH:15]=[N:16][C:17]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:24]([NH:39][CH:38]5[CH2:34][CH2:32][N:31]([CH3:30])[CH2:35][CH2:37]5)=[O:26])=[CH:27][CH:28]=4)=[N:18][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 235274-(Aminomethyl)piperidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 25123680HCID 25123680, compound

Product 1

HCID 25123681HCID 25123681, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(9-Cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-benzoic acid (35 mg, 0.085 mmol), DIPEA (28 μl, 0.17 mmol, 2 eq) and TBTU (30 mg, 0.093 mmol, 1.1 eq) were added to 3 ml DCM and the resulting solution stirred at rt for 30 min before the addition of 4-aminomethylpiperidine (13 μl, 0.10 mmol, 1.2 eq). The RM was then stirred at rt for 16h. The RM was concentrated and the product extracted using DCM/H2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give a yellow oily residue (21 mg, 49%); Rt=9.86 min (0—60—20 min, purity 100%); 1H NMR (CD3OD): δ 1.69-1.75 (m, 6H), 1.82 (bs, 2H), 1.96-1.99 (m, 2H), 2.03-2.05 (bs, 2H), 2.18-2.23 (m, 2H), 2.34 (s, 3H, CH3), 2.68 (dd, J=4.5 Hz, 2H, CH2), 2.95-2.97 (m, 2H), 3.28 (s, 3H, CH3), 3.73 (dd, J=4.5 Hz, 2H, CH2), 3.89-3.94 (m, 1H, CH), 4.01 (s, 3H, CH3), 4.91-4.96 (m, 1H, CH), 7.49-7.51 (m, 2H), 8.02 (bs, 1H), 8.50 (d, J=8.5 Hz, 1H, phe-H); MS+ve: 508.2.

Workup

  1. concentrationThe RM was concentrated
  2. extractionthe product extracted
  3. washwashed with sat NaCl
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customfurther dried in vacuo

Sources & evidence

ORD record
ord-bc8e9b758e714412a78399dfb9ce9d59
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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