Tris(hydroxymethyl)aminomethane → HCID 178520572, compound

HRID 2415616Notes

Reaction equation

HRID 2415616 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N=C=N.C1C=CC2N(O)N=NC=2C=1.[Cl:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32]([NH:38][CH:39]3[CH2:44][CH2:43][CH:42]([NH2:45])[CH2:41][CH2:40]3)=[CH:33][CH:34]=[N:35]2)=[CH:30][CH:29]=1.C(O)C(N)(CO)CO>CN(C=O)C>[Cl:27][C:28]1[CH:37]=[C:36]2[C:31]([C:32]([NH:38][C@@H:39]3[CH2:40][CH2:41][C@H:42]([NH:45][C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:43][CH2:44]3)=[CH:33][CH:34]=[N:35]2)=[CH:30][CH:29]=1

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 16757Benzenepentanoic acidHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

Product 1

HCID 178520572HCID 178520572, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

31 mg (0.16 mmol) of 5-phenylvaleric acid, 112 mg (0.22 mmol) of PS-carbodiimide and 28 mg (0.18 mmol) HOBT in DMF (1 mL) were mixed for 15 min. 30 mg (0.11 mmol) of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine was added and the reaction was allowed to proceed overnight. 116 mg (0.54 mmol) of PS-trisamine was added and the reaction mixture was filtered after two hours. The solvent was evaporated and the product was purified by reverse phase HPLC to provide the titled compound. MS (ESI(+)) m/e 436 (M+H)+; 1H NMR (500 MHz, DMSO) δ ppm 13.86 (brs, 1 H), 8.82 (d, 1 H), 8.72 (d, 1 H), 8.54 (d, 1 H), 7.94 (d, 1 H), 7.78 (dd, 1 H), 7.69 (d, 1 H), 7.21 (m, 5 H), 6.96 (d, 1 H), 3.89 (m, 1 H), 3.80 (m, 1 H), 2.58 (m, 2 H), 2.50 (m, 2 H), 2.16 (m, 2 H), 1.82 (m, 6 H), 1.47-1.70 (m, 6 H).

Workup

  1. filtrationthe reaction mixture was filtered after two hours
  2. customThe solvent was evaporated
  3. customthe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ff3dda64e62b4321a6e42ccb2ce5436c
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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