Triethylamine → HCID 54689839, compound

HRID 1244116Notes

Reaction equation

HRID 1244116 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]2[S:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[CH:15][CH:14]=3)[C:5]=2[C:4]=1[OH:28])#[N:2].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:61][CH2:62][N:63](CC)[CH2:64][CH3:65]>CN(C=O)C>[CH2:62]([N:63]([CH2:64][CH3:65])[C:25](=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21][C:20]#[C:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]2[C:5]3[C:4]([OH:28])=[C:3]([C:1]#[N:2])[C:8](=[O:9])[NH:7][C:6]=3[S:10][CH:11]=2)=[CH:18][CH:17]=1)[CH3:61]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 54689836HCID 54689836, compound

Product 1

HCID 54689839HCID 54689839, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-[4-(5-cyano-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridin-3-yl)-phenyl]-hept-6-ynoic acid (24 mg, 0.06 mmol) in 0.5 mL DMF was added HOBT (trace) followed by TBTU (23 mg, 0.07 mmol). The pH of the reaction mixture was adjusted to pH>6 using Et3N, then stirred at rt overnight. Solvent was removed in vacuo, the resulting slurry was redissolved in MeOH and purified using reverse phase HPLC to afford the titled compound. MS (ESI) m/e 448 (M+H)+; 1H NMR (400 MHz, DMSO-d6): δ 1.00 (t, J=8.1 Hz, 3H), 1.10 (t, J=8.1 Hz, 3H), 1.58–1.68 (m, 4H), 2.33 (t, J=6.90 Hz, 2H), 2.45 (t, J=6.90 Hz, 2H), 3.23–3.33 (m, 4H), 6.65 (s, 1H), 7.26 (d, J=8.59 Hz, 2H), 7.42 (d, J=8.59 Hz, 2H).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe resulting slurry was redissolved in MeOH
  3. custompurified

Sources & evidence

ORD record
ord-40940afcd83d4b878ef21a203625d751
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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