Tris(hydroxymethyl)aminomethane → HCID 69308498, compound

HRID 2250134Notes

Reaction equation

HRID 2250134 reaction equation
Cl.Cl.N1([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH2:19][NH:18][CH2:17][CH2:16]3)CCCCC1.CC[N:25]([CH:29]([CH3:31])C)[CH:26]([CH3:28])C.[CH:32]([N:35]=[C:36]=[O:37])([CH3:34])[CH3:33].[CH2:38](O)C(N)(CO)CO.[N-]=C=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:32]([NH:35][C:36]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([O:12][CH2:11][CH:10]([N:25]3[CH2:26][CH2:28][CH2:38][CH2:31][CH2:29]3)[CH3:9])[CH:14]=2)[CH2:19]1)=[O:37])([CH3:34])[CH3:33]

Participants

8

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 69308514HCID 69308514, compound

Product 1

HCID 69308498HCID 69308498, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 4 mL vial is placed 6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-isoquinoline dihydrochloride (25.0 mg, 0.07 mmol), resin-bound Hunigs base (81 mg, 0.29 mmol, 3.54 mmol/g), resin bound DMAP (catalytic), and dry CH2Cl2 and isopropyl isocyanate (16□L, 0.18 mmol). The vial is agitated by means of a lab quake shaker overnight. In the morning, PS-trisamine (120 mg, 0.36 mmol, 3.0 mmol/g) is added and the reaction again allowed to rotate for 4 hours to scavenge excess isocyanate., Filtration, washing with CH2Cl2 and concentration afforded the desired urea. M+1 360.

Workup

  1. customthe reaction
  2. waitto rotate for 4 hours
  3. filtration, Filtration
  4. washwashing with CH2Cl2 and concentration

Sources & evidence

ORD record
ord-609a4283eafc4653be07eb6b555c9353
Source dataset
uspto-grants-2008_01
Patent number
US07314937B2

Reaction notes

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