Tris(hydroxymethyl)aminomethane → HCID 59525958, compound

HRID 385828Notes

Reaction equation

HRID 385828 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.C1C=CC2N(O)N=NC=2C=1.[NH2:23][C:24]([C:26]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([OH:40])([CH3:39])[CH3:38])=[CH:33][C:32]=2[F:41])[S:28][C:27]=1[NH:42][C:43]1[N:48]=[C:47]([CH2:49][N:50]([CH2:61][C:62]([OH:64])=O)[C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:52])[CH:46]=[CH:45][CH:44]=1)=[O:25].[CH3:65][NH:66][CH2:67][CH2:68][OH:69].[N-]=C=O.C(O)C(N)(CO)CO>C(Cl)Cl.CN(C=O)C>[CH2:54]([O:53][C:51](=[O:52])[N:50]([CH2:49][C:47]1[CH:46]=[CH:45][CH:44]=[C:43]([NH:42][C:27]2[S:28][C:29]([C:31]3[CH:36]=[CH:35][C:34]([C:37]([OH:40])([CH3:38])[CH3:39])=[CH:33][C:32]=3[F:41])=[CH:30][C:26]=2[C:24]([NH2:23])=[O:25])[N:48]=1)[CH2:61][C:62]([N:66]([CH2:67][CH2:68][OH:69])[CH3:65])=[O:64])[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

9

Reactant 6

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 80162-(Methylamino)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 59526203HCID 59526203, compound

Product 1

HCID 59525958HCID 59525958, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of PS-CDI (152 mg, 0.19 mmol), HOBt (14 mg, 0.091 mmol), {{[6-({3-(Aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]methyl}[(benzyloxy)carbonyl]amino}acetic acid (45 mg, 0.076 mmol) and 2-(methylamino)ethanol (7.0 mg, 0.091 mmol) in 2:1 mixture of DCM (1.6 mL) and DMF (0.8 mL) was heated to 100° C. under the microwave irradiation for 5 min. Upon cooling, MP-isocyanate (241 mg, 0.30 mmol), PS-trisamine (89 mg, 0.30 mmol) and 1 mL DCM were added to a reaction mixture and heated to 100° C. under the microwave irradiation for 10 min. The reaction mixture was filtered, washed with DCM, and concentrated in vacuo to afford the title compound.

Workup

  1. temperatureUpon cooling
  2. temperatureheated to 100° C. under the microwave irradiation for 10 min
  3. filtrationThe reaction mixture was filtered
  4. washwashed with DCM
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bd9524449dc48a9ac5abd55fd558699
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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