Sodium Bicarbonate → HCID 53627623, compound

HRID 1715923Notes

Reaction equation

HRID 1715923 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[S:22][N:21]=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[F:23][C:24]([F:39])([F:38])[C:25]1[CH:33]=[C:32]2[C:28]([CH2:29][CH2:30][N:31]2[CH2:34][C:35](O)=[O:36])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C>[O:1]=[C:2]1[CH2:7][N:6]([C:35](=[O:36])[CH2:34][N:31]2[C:32]3[C:28](=[CH:27][CH:26]=[C:25]([C:24]([F:38])([F:23])[F:39])[CH:33]=3)[CH2:29][CH2:30]2)[CH2:5][CH2:4][N:3]1[C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][C:18]2[S:22][N:21]=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59466056HCID 59466056, compoundHCID 67082755HCID 67082755, compound

Product 1

HCID 53627623HCID 53627623, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Synthesized according to general procedure 14, method B. The reaction was set up with 4-(2-oxopiperazin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (50 mg, 0.15 mmol), 2-(6-(trifluoromethyl)indolin-1-yl)acetic acid (25 mg, 0.10 mmol), HATU reagent (76 mg, 0.20 mmol), sodium bicarbonate (17 mg, 0.20 mmol), and DMF (0.20 mL) to obtain the desired amide as a white solid (50 mg, 0.10 mmol, 32% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=565.0; tR=2.91 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-babbc2e3f089489a8eb31da9817ee481
Source dataset
uspto-grants-2010_09
Patent number
US07799822B2

Reaction notes

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