Ethanolamine → HCID 59526349, compound

HRID 385825Notes

Reaction equation

HRID 385825 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][CH2:25][CH2:26][OH:27].C1C=CC2N(O)N=NC=2C=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[N:18]=1)[CH2:12][C:13]([NH:24][CH2:25][CH2:26][OH:27])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 700EthanolamineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 682631,1'-CarbonyldiimidazoleHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 59526017HCID 59526017, compound

Product 1

HCID 59526349HCID 59526349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-[(benzyloxy)carbonyl]-N-[(6-bromopyridin-2-yl)methyl]glycine (Example 179, Step 3) (112 mg, 0.295 mmol), 2-aminoethanol (18 μL, 0.295 mmol), HOBt (59 mg, 0.325 mmol) and PS-CDI (586 mg, 0.732 mmol) in DCM (4.0 mL) was irradiated in the microwave at 100° C. for 5 min. To this mixture, MP-isocyanate (967 mg, 1.22 mmol), PS-trisamine (393 mg, 1.34 mmol) and DCM (5.0 mL) were added and irradiated in the microwave at 100° C. for 10 min. The reaction mixture was filtered, washed with DCM and the filtrate was concentrated in vacuo to afford the title compound as a clear oil.

Workup

  1. customwas irradiated in the microwave at 100° C. for 5 min
  2. customirradiated in the microwave at 100° C. for 10 min
  3. filtrationThe reaction mixture was filtered
  4. washwashed with DCM
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-626afe4a33f34a119d5e2e05f7dbd948
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

Loading…