4-(Aminomethyl)piperidine → HCID 25123681, compound

HRID 1044077Notes

Reaction equation

HRID 1044077 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 16 h. 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-d871e0c3678b4ed7acd33080ea85bfff
Source dataset
uspto-grants-2013_10
Patent number
US08563542B2

Reaction notes

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