Sodium Bicarbonate → HCID 59465931, compound

HRID 2043129Notes

Reaction equation

HRID 2043129 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]3[S:22][N:21]=[CH:20][N:19]=3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.[Cl:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[N:31]([CH2:33][C:34](O)=[O:35])[CH:30]=[CH:29]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+].Cl.S1C(N)=NC=N1>>[Cl:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:32]=1[N:31]([CH2:33][C:34]([N:7]1[CH2:6][CH2:5][N:4]([C:8]3[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]4[S:22][N:21]=[CH:20][N:19]=4)(=[O:16])=[O:15])=[CH:10][CH:9]=3)[CH2:3][C@H:2]1[CH3:1])=[O:35])[CH:30]=[CH:29]2

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 59465674(r)-4-(3-Methylpiperazin-1-yl)-n-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 670826997-Chloro-indole-1-acetic acid

Product 1

HCID 59465931HCID 59465931, compoundYield 288.7%

Procedure

Synthesized according to general procedure 9, method B. The reaction was set up with (R)-4-(3-methylpiperazin-1-yl)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (400 mg, 1.2 mmol), 2-(7-chloro-1H-indol-1-yl)acetic acid (250 mg, 0.15 mmol), HATU reagent (390 mg, 0.15 mmol), sodium bicarbonate (151 mg, 1.8 mmol), and DMF/CH2Cl2—1/1 (1.0 mL) to obtain the desired amide as a white solid (230 mg, 36% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=531.0; tR=3.21 min.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-0a12a576a2b04e8ca0e5bd64198736be
Source dataset
uspto-grants-2013_11
Patent number
US08586589B2

Reaction notes

Loading…