Tris(hydroxymethyl)aminomethane → HCID 54689850, compound

HRID 1244127Notes

Reaction equation

HRID 1244127 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[NH:7][CH:6]2[S:10][CH:11]=[C:12]([C:13]3[CH:25]=[CH:24][C:16]([CH:17]=[N:18][O:19][CH2:20][C:21]([OH:23])=O)=[CH:15][CH:14]=3)[CH:5]2[C:4]=1[OH:26])#[N:2].[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH2:34].C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.C(O)C(N)(CO)CO>ClCCl.CN(C)C(=O)C>[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]2[S:10][CH:11]=[C:12]([C:13]3[CH:14]=[CH:15][C:16](/[CH:17]=[N:18]/[O:19][CH2:20][C:21]([NH:34][CH2:33][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=4)=[O:23])=[CH:24][CH:25]=3)[C:5]=2[C:4]=1[OH:26])#[N:2]

Participants

7

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 10868DicyclohexylcarbodiimideHCID 195092-PyridinemethanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 76171765HCID 76171765, compound

Product 1

HCID 54689850HCID 54689850, compound

Reagents, catalysts & solvents 1

HCID 85741463dichloromethane N,N-dimethylacetamideSolvent

Procedure

[4-(5-Cyano-4-hydroxy-6-oxo-3a,6,7,7a-tetrahydro-thieno[2,3-b]pyridin-3-yl)-benzylideneaminooxy]-acetic acid (0.035 g, 0.1 mmol) and C-pyridin-2-yl-methylamine (0.013 g, 0.12 mmol) were added to a suspension of resin bound 1,3-dicyclohexyl carbodiimide (0.166 g, 1.2 mmol/g, 0.2 mmol) and 1-hydroxybenzotriazole hydrate (0.013 g, 0.1 mmol) in 1:1 dichloromethane/N,N-dimethylacetamide (4 mL) at room temperature. After complete reaction, resin bound trisamine (4.7 mmol/g, 0.053 g, 0.25 mmol) was added to the reaction mixture, shaken at room temperature for 1 hour, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 457.8 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 12.15 (br s, 1H), 8.52–8.56 (m, 2H), 8.42 (s, 1H), 7.88 (dt, J=10.5, 1H), 7.61 (d, J=10, 2H), 7.51 (d, J=10, 2H), 7.38–7.43 (m 2H), 7.01 (s, 1H), 4.65 (s, 2H), 4.50 (d, J=5, 1H).

Workup

  1. customat room temperature
  2. additionwas added to the reaction mixture
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-76091b2cf53c43e7b18ffa6796f893bc
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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