Formaldehyde → HCID 11212985、化合物

HRID 1987247ノート

反応式

HRID 1987247 の反応式
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

参加物

8

反応物 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11292979HCID 11292979、化合物

生成物 1

HCID 11212985HCID 11212985、化合物収率 27.8%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 21877088Acetonitrile methylene chloride溶媒

実験手順

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 (acetonitrile/water, 0.05% TFA) 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 Hz, 1.0 Hz, 1H), 8.18 (dd, J=8.8 Hz, 1.0 Hz, 1H), 7.63 (dd, J=8.8 Hz, 7.0 Hz, 1H), 6.95 (d, J=2.5 Hz, 7 Hz, 1H), 6.90 (d, J=8.7 Hz, 1H), 6.26 (dd, 8.7 Hz, 2.5 Hz, 1H), 3.16 (s, 4H), 2.95 (s, 6H), 1.56 (m, 2H), 1.42 (m, 4H).

後処理

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

出典と根拠

ORDレコード
ord-00830f6cedba45b696959c4550a7fd5f
出典データセット
uspto-grants-2009_06
特許番号
US07550492B2

反応ノート

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