Formaldehyde → HCID 11212985, 화합물

HRID 1294632노트

반응식

HRID 1294632 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 11212985HCID 11212985, 화합물수율 27.8%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 21877088Acetonitrile methylene chloride용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5eb97ca6159b4e05a106f32b3ed82f34
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241759B2

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