Dimethylformamide → HCID 131734804, compound

HRID 1778149Notes

Reaction equation

HRID 1778149 reaction equation
[CH3:1][S@:2]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[NH:4])=[O:3].[NH2:13][C:14]1[C:22]([C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([C:34]3[O:35][CH:36]=[CH:37][C:38]=3C)=[O:33])[CH:26]=2)=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][N:15]=1.C(N([CH:46]([CH3:48])C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:59]=2N=N1.CN([CH:79]=[O:80])C>CCOC(C)=O>[NH2:13][C:14]1[N:15]=[CH:16][C:17]([C:18]([N:4]=[S@@:2]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])([CH3:1])=[O:3])=[O:19])=[CH:21][C:22]=1[C:23]#[C:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[O:33])[C:34]2[CH:48]=[CH:46][C:36]([O:35][CH3:59])=[C:37]([O:80][CH3:79])[CH:38]=2)[CH:26]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576578956-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acidHCID 118130115HCID 118130115, compound

Product 1

HCID 131734804HCID 131734804, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of (S)-methyl 5-(S-methylsulfonimidoyl)pentanoate, (130 mg, 0.672 mmol, 1.2 eq) in anhydrous DMF (3 mL) was added 6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinic acid, (200 mg, 0.554 mmol, 1.0 eq), diisopropylethyl amine (0.2 mL, 2.0 eq), and BOP (270 mg, 1.1 eq). After the reaction solution was heated at 60° C. for three hours, it was cooled to room temperature, diluted with EtOAc, washed with aqueous NH4Cl, water, brine, and lastly dried with anhydrous sodium sulfate. The clear solution was decanted, concentrated, and the brown oily residue was subject to column chromatography (EtOAc-Hex from 1:4 to 6:1). The corresponding product fractions were collected, concentrated under reduced pressure, and the residue was triturated with EtOAc-Hex (1:9). The solid which formed by scratching was collected by filtration and dried to give the title compound as a white solid (155 mg).

Workup

  1. temperatureit was cooled to room temperature
  2. washwashed with aqueous NH4Cl, water, brine
  3. dry with materiallastly dried with anhydrous sodium sulfate
  4. customThe clear solution was decanted
  5. concentrationconcentrated
  6. customThe corresponding product fractions were collected
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was triturated with EtOAc-Hex (1:9)
  9. customThe solid which formed
  10. filtrationby scratching was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-4d0cc8cd17774d2b8ea06a3405a7a242
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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