Hydrochloric Acid → HCID 131737051, compound

HRID 58998Notes

Reaction equation

HRID 58998 reaction equation
[C:1]1(C2C=CC=CC=2)[CH2:2][C:3](CNCCCNCCCNCC(C)C)([CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:4]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH:6]=1.[ClH:55]>>[ClH:55].[C:1]1([C:1]2[CH:2]=[CH:3][CH:4]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH:6]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH:4]=[C:3]([CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH:2]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131737052N1,N1',N1''-([1,1'-Biphenyl]-3,3,5-triyltris(methylene))tris(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

Product 1

HCID 131737051HCID 131737051, compoundYield 52%

Procedure

N1,N1′,N1″-([1,1′-biphenyl]-3,3′,5-triyltris(methylene))tris(N3-(3-(isobutylamino)propyl)propane-1,3-diamine) from step 2 was subjected to acidification with methanolic HCl (100 mL, 1.0M). The reaction mixture stirred at rt for 2 h. The reaction mixture was concentrated under reduced pressure and the solid was collected by vacuum filtration and washed with Et2O (50 mL) and hot MeOH (50 mL) to afford the desired product (0.58 g, 52%) as a white solid. 1H NMR (500 MHz, D2O) δ ppm 7.91 (s, 1H), 7.85-7.82 (m, 3H), 7.65-7.56 (m, 3H), 4.42 (s, 4H), 4.39 (s, 2H), 3.29-3.16 (m, 24H), 2.93 (d, J=6.0 Hz, 6H), 2.20-2.13 (m, 12H), 2.07-2.00 (m, 3H), 0.99 (d, J=6.0 Hz, 18H). 13CNMR (125 MHz, D2O) δ ppm 141.6, 139.8, 132.2, 131.3, 130.4, 130.3, 129.7, 129.5, 128.6, 128.4, 54.8, 54.8, 51.1, 50.8, 44.7, 44.6, 44.2, 44.0, 25.5, 22.7, 22.5, 19.0. LRMS [M+2H+]2+376.8.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe solid was collected by vacuum filtration
  3. washwashed with Et2O (50 mL) and hot MeOH (50 mL)

Sources & evidence

ORD record
ord-975bbb9cc65c4648a561d230b49aaa64
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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