Tris(hydroxymethyl)aminomethane → HCID 74221662, compound

HRID 2202545Notes

Reaction equation

HRID 2202545 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=[CH:2]1.N=C=N.C1C=CC2N(O)N=NC=2C=1.[NH2:22][C@H:23]([C:33]1[NH:34][C:35]([C:38]2[C:39]([O:48][CH3:49])=[N:40][C:41]3[C:46]([CH:47]=2)=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:36][N:37]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=[O:30].C(O)C(N)(CO)CO>C(Cl)Cl.CN(C=O)C>[CH3:49][O:48][C:39]1[C:38]([C:35]2[NH:34][C:33]([C@@H:23]([NH:22][C:6]([C:5]3[S:1][CH:2]=[N:3][CH:4]=3)=[O:8])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][CH3:32])=[O:30])=[N:37][CH:36]=2)=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:40]=1

Participants

8

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 84494Thiazole-5-carboxylic acidHCID 160435CarbodiimideHCID 90149563HCID 90149563, compound

Product 1

HCID 74221662HCID 74221662, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A glass tube was charged with thiazole-5-carboxylic acid (1.5 eq.), PS-carbodiimide resin (2 eq.), HOBt (1.7 eq.) and diluted with DCM (0.04 M). The tube was capped and stirred on a rotor for 10 min. Then, a solution of A4 in DMF (0.06 M) was added and the reaction mixture was stirred in a rotor for 24 h. After addition of MP-Trisamine resin (10 eq.) the reaction was stirred for additional 24 h. The resulting reaction mixture was filtered through a fritted syringe and washed with DCM. The combined organic solutions were concentrated under reduced pressure to give the title compound. MS (ES+) C25H28N6O3S: 493 (M+H)+.

Workup

  1. customThe tube was capped
  2. stirringthe reaction mixture was stirred in a rotor for 24 h
  3. stirringwas stirred for additional 24 h
  4. customThe resulting reaction mixture
  5. filtrationwas filtered through a fritted syringe
  6. washwashed with DCM
  7. concentrationThe combined organic solutions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-234deb321a994465b9627e22ab5299fc
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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