Sodium Bicarbonate → HCID 53627616, compound

HRID 1696112

Reaction equation

HRID 1696112 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:19][CH:20]=[CH:21][N:22]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.F[C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[CH:29][N:30]2[C:33]([CH3:38])([CH3:37])[C:34](O)=[O:35])=[CH:26][CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:56][P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+].Cl.S1C(N)=NC=N1>>[F:56][C:26]1[CH:25]=[CH:24][CH:32]=[C:31]2[C:27]=1[CH:28]=[CH:29][N:30]2[C:33]([CH3:38])([CH3:37])[C:34]([N:6]1[CH2:5][CH2:4][N:3]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)(=[O:16])=[O:15])=[CH:12][CH:13]=2)[C:2](=[O:1])[CH2:7]1)=[O:35]

Participants

6

Reactant 5

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 220145431,2,4-Thiadiazol-5-amine--hydrogen chloride (1/1)HCID 594656314-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamideHCID 67082747HCID 67082747, compound

Product 1

HCID 53627616HCID 53627616, compoundYield 34.5%

Procedure

Synthesized according to general procedure 14, method A. The reaction was set up with 4-(2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (100 mg, 0.29 mmol), 2-(6-fluoro-1H-indol-1-yl)-2-methylpropanoic acid (66 mg, 0.29 mmol), HATU reagent (220 mg, 0.58 mmol), sodium bicarbonate (74 mg, 0.87 mmol), and DMF/CH2Cl2-1/1 (0.50 mL) to obtain the desired amide as a white solid (50 mg, 0.10 mmol, 32% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.76 (s, 1H), 7.71 (d, J=8.5 Hz, 2H), 7.66 (s, 1H), 7.27-6.91 (m, 5H), 6.90-6.82 (m, 2H), 6.68 (d, J=3.0 Hz, 1H), 4.23 (s, 1H), 3.87 (bs, 1H), 3.57 (bs, 1H), 3.42-3.35 (m, 1H), 3.06 (s, 1H), 2.89 (s, 1H), 1.81 (d, J=8.3 Hz, 6H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=542.5; tR=2.91 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-d5562a0fe226469fa09fccf79da450dd
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Linked notes

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