Formaldehyde → HCID 11212985, compound

HRID 1294632Notes

Reaction equation

HRID 1294632 reaction equation
N[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.[CH2:29]=O.[C:31]([BH3-])#[N:32].[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C.C(#N)C.C(Cl)Cl>[CH3:29][N:32]([CH3:31])[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

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11292979HCID 11292979, compound

Product 1

HCID 11212985HCID 11212985, compoundYield 27.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a stirred solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-amino-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 24; 30 mg, 0.072 mmol) in 2:1 acetonitrile/DCM (6 mL), was added formaldehyde (0.1 mL, 3.6 mmol), sodium cyanoborohydride (68 mg, 1.08 mmol) and acetic acid (12 μL). The reaction mixture was stirred for 3 h at room temperature. 1 M NaOH was added until the solution became basic. The mixture was taken up in DCM (5 mL), and washed with water and brine. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC to afford the title compound (8 mg, 0.02 mmol, 25%). MS (ESI): m/z 446 [M+H]+, 468 [M+Na]+. HPLC (reversed-phase): RT=9.14 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.61 (s, 1H), 8.22 (dd, J=7.0, 1.0 Hz, 1H), 8.18 (dd, J=8.8, 1.0 Hz, 1H), 7.63 (dd, J=8.8, 7.0 Hz, 1H), 6.95 (d, J=7.0, 2.5 Hz, 1H), 6.90 (d, J=8.7 Hz, 1H), 6.26 (dd, 8.7, 2.5 Hz, 1H), 3.16 (s, 4H), 2.95 (s, 6H), 1.56 (m, 2H), 1.42 (m, 4H).

Workup

  1. washwashed with water and brine
  2. customThe organic layer was removed
  3. customdried
  4. custompurified by preparative reversed-phase HPLC

Sources & evidence

ORD record
ord-5eb97ca6159b4e05a106f32b3ed82f34
Source dataset
uspto-grants-2007_07
Patent number
US07241759B2

Reaction notes

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