Diisopropylethylamine → HCID 67208668, compound

HRID 711220Notes

Reaction equation

HRID 711220 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:30][CH2:29][C:26]3[CH:27]=[N:28][C:23]([N:20]4[CH2:21][CH2:22][S:17][CH2:18][CH2:19]4)=[CH:24][CH:25]=3)=[O:16])=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27826864-(3-fluorophenyl)benzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43528580HCID 43528580, compound

Product 1

HCID 67208668HCID 67208668, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3′-fluorobiphenyl-4-carboxylic acid 8-5 (51 mg, 0.24 mmol), (6-thiomorpholinopyridin-3-yl)methanamine 8-4 (45 mg, 0.21 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (91 mg, 0.24 mmol) in DMF (1.0 mL) was added DIEA (0.1 mL, 0.64 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give 3′-fluoro-N-((6-thiomorpholinopyridin-3-yl)methyl)biphenyl-4-carboxamide 8-6. MS m/z 408.2 (M+1).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-ff5a067dd1884e4f889e6f50b1f15def
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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