Dimethylformamide → HCID 45138254, compound

HRID 2278758Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[CH:13]=[C:12]([C:23]([OH:25])=O)[CH:11]=1)#[N:2].[NH2:26][C@@H:27]([CH3:30])[CH2:28][OH:29].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[OH:29][CH2:28][C@@H:27]([NH:26][C:23]([C:12]1[CH:11]=[C:10]([C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[C:1]#[N:2])[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[CH:13]=1)=[O:25])[CH3:30]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 80307L-Alaninol

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 67304332HCID 67304332, compound

Product 1

HCID 45138254HCID 45138254, compound

Procedure

A round bottom flask was charged with 2′-cyano-5′-methyl-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid (30.0 mg, 0.0914 mmol), (2S)-2-Aminopropan-1-ol (13.724 mg, 0.18272 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.14474 g, 0.38068 mmol), N,N-diisopropylethylamine (0.10609 mL, 0.60908 mmol), N,N-dimethylformamide (0.260 mL, 3.35 mmol) and the reaction stirred over night at room temperature. The solvent was removed under reduced pressure and the residue purified by prep HPLC to get the compound as white solid.

Workup

customThe solvent was removed under reduced pressure
customthe residue purified by prep HPLC

Sources & evidence

ORD record: ord-173244989b11415ba88c057e68555862
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133122B2

Reaction notes

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