1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10093336, compound

HRID 966146Notes

Reaction equation

HRID 966146 reaction equation
[F:1][C:2]1[C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH:19]([CH3:21])[CH3:20])[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[O:60]([NH2:62])[CH3:61].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[F:1][C:2]1[C:25]([C:26]([NH:62][O:60][CH3:61])=[O:28])=[CH:24][CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH:19]([CH3:21])[CH3:20])[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86591632HCID 86591632, compound

Product 1

HCID 10093336HCID 10093336, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-fluoro-3-carboxyphenoxy]-5-(1-methylethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid, ethyl ester (14 mg, 0.036 mmol) in dimethyl formamide at RT were added EDCI (14 mg, 0.07 mmol), DIPEA (20 μL, 0.11 mmol), HOBt (9.7 mg, 0.07 mmol), and methoxylamine hydrochloride (6 mg, 0.07 mmol). After stirring overnight, HPLC analysis revealed that only 10% product was formed. BOP reagent (0.1 mmol) was added. After 6 h, all the starting material was consumed. The mixture was purified by reverse phase preparative HPLC to afford the desired product (14 mg, 93%). LC/MS: (M+H)+=417.

Workup

  1. customwas formed
  2. waitAfter 6 h
  3. customall the starting material was consumed
  4. customThe mixture was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-a6e14c782c514f239a0f814b3848fb59
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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