Sodium Bicarbonate → HCID 53627630, compound

HRID 1876690Notes

Reaction equation

HRID 1876690 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([OH:14])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:39][C:40]1([C:46]2[CH:51]=[CH:50][C:49]([S:52]([NH:55][C:56]3[S:57][CH:58]=[CH:59][N:60]=3)(=[O:54])=[O:53])=[CH:48][CH:47]=2)[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]([N:43]2[CH2:42][CH2:41][C:40]([C:46]3[CH:51]=[CH:50][C:49]([S:52]([NH:55][C:56]4[S:57][CH:58]=[CH:59][N:60]=4)(=[O:53])=[O:54])=[CH:48][CH:47]=3)([OH:39])[CH2:45][CH2:44]2)=[O:14])=[CH:4][CH:3]=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 28284423(6-CHLORO-INDOL-1-YL)-ACETIC ACIDHCID 59465917HCID 59465917, compound

Product 1

HCID 53627630HCID 53627630, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared using general procedure 20. A solution of 2-(6-chloro-1H-indol-1-yl)acetic acid (184 mg, 0.88 mmol) and HATU (335 mg, 0.88 mmol) in DMF (3 mL) was stirred under an N2 atmosphere at 0° C. for 1 h. To this mixture, 4-(4-hydroxypiperidin-4-yl)-N-(thiazol-2-yl)benzenesulfonamide (300 mg, 0.88 mmol) and NaHCO3 (148 mg, 1.76 mmol) were added under an N2 atmosphere at RT, and the reaction was stirred for 16 h. The reaction mixture was filtered and purified by Gilson preparative HPLC (5-99% CH3CN—H2O) to isolate 4-(1-(2-(6-chloro-1H-indol-1-yl)acetyl)-4-hydroxypiperidin-4-yl)-N-(thiazol-2-yl)benzenesulfonamide (246 mg, 52%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=531.3; tR=2.98 min. 1H NMR (400 MHz, DMSO-d6) 8, 7.78 (d, J=8.5 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 7.29 (dd, J=28.5, 3.9 Hz, 2H), 7.03 (dd, J=9.3, 0.9 Hz, 1H), 6.83 (d, J=4.6 Hz, 1H), 6.47 (d, J=3.1 Hz, 1H), 5.23 (q, J=14.8 Hz, 2H), 4.27 (d, J=12.1 Hz, 1H), 3.87 (d, J=12.6 Hz, 1H), 3.51 (t, J=11.9 Hz, 1H), 3.02 (t, J=11.6 Hz, 1H), 2.04-1.97 (m, 1H), 1.81 (m, 1H), 1.67-1.61 (m, 2H).

Workup

  1. customPrepared
  2. filtrationThe reaction mixture was filtered
  3. custompurified by Gilson preparative HPLC (5-99% CH3CN—H2O)

Sources & evidence

ORD record
ord-b5c623bc6905411cb85a505010dca6bc
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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