Sodium Hydroxide → HCID 11295248, compound

HRID 1987248Notes

Reaction equation

HRID 1987248 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3=[N:18][S:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.[CH:29]1([CH:35]=O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C.C(Cl)Cl>[CH:29]1([CH2:35][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:21]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[O:22])=[C:6]([NH:8][S:9]([C:12]3[C:17]4=[N:18][S:19][N:20]=[C:16]4[CH:15]=[CH:14][CH:13]=3)(=[O:11])=[O:10])[CH:7]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11292979HCID 11292979, compound

Product 1

HCID 11295248HCID 11295248, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-amino-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 24; 50 mg, 0.12 mmol) in dichloroethane (4 mL) was added cyclohexanecarboxaldehyde (43 μL, 0.36 mmol), followed by sodium triacetoxyborohydride (50 mg, 0.24 mmol). The reaction mixture was stirred for 12 h at room temperature. 1 M NaOH was added until the solution became basic. The mixture was taken up in 5 mL of DCM and washed with water and aqueous NaHCO3. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC (acetonitrile/water, 0.05% TFA) to afford the title compound (20 mg, 0.04 mmol, 33%). MS (ESI): m/z 514 [M+H]+, 536 [M+Na]+. HPLC (reversed-phase): RT=10.93 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.36 (s, 1H), 8.20 (dd, J=8.8 Hz, 7.0 Hz, 2H), 7.63 (dd, J=8.8 Hz, 7.0 Hz, 1H), 6.85 (d, J=3.8 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 6.15 (dd, J=8.5 Hz, 2.3 Hz, 1H), 3.21 (m, 4H), 2.90 (d, J=6.7 Hz, 2H), 1.74 (m, 6H), 1.57 (m, 2H), 1.46 (m, 4H), 1.22 (m, 3H), 0.96 (m, 2H).

Workup

  1. washwashed with water and aqueous NaHCO3
  2. customThe organic layer was removed
  3. customdried
  4. custompurified by preparative reversed-phase HPLC (acetonitrile/water, 0.05% TFA)

Sources & evidence

ORD record
ord-c1b85d835ba745658eab88ab180d201d
Source dataset
uspto-grants-2009_06
Patent number
US07550492B2

Reaction notes

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