Dimethylformamide → HCID 45138696, compound

HRID 2278765Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16](O)=[O:17])[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][OH:26])[CH:11]=1)#[N:2].[NH2:27][C@@H:28]([CH3:31])[CH2:29][OH:30].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:30][CH2:29][C@@H:28]([NH:27][C:16]([C:14]1[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][OH:26])[CH:11]=[C:10]([C:4]2[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:3]=2[C:1]#[N:2])[CH:15]=1)=[O:17])[CH3:31]

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 67387723HCID 67387723, compound

Product 1

HCID 45138696HCID 45138696, compound

Procedure

A reaction vial was charged with 2-Cyano-2″-hydroxymethyl-4-methyl-[1,1′;3′,1″]terphenyl-5′-carboxylic acid (50.00 mg, 0.1456 mmol), (2S)-2-aminopropan-1-ol (13.12 mg, 0.1747 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (110.7 mg, 0.2912 mmol), N,N-diisopropylethylamine (0.06341 mL, 0.3640 mmol) and N,N-dimethylformamide (5.0 mL, 64 mmol) and the reaction stirred at room temperature over night. The reaction mixture was then purified by prep HPLC to get the compound as white solid.

Workup

customA reaction
customThe reaction mixture was then purified by prep HPLC

Sources & evidence

ORD record: ord-f0ec5a9eef5c4b468f1e1c646cc83e33
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133122B2

Reaction notes

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