Aminoacetaldehyde dimethyl acetal → 4-Amino-N-(2,2-dimethoxyethyl)-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridine-7-carboxamide

HRID 17208

반응식

HRID 17208 반응식
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32](O)=[O:33])=[CH:4][N:3]=1.[CH3:35][O:36][CH:37]([O:40][CH3:41])[CH2:38][NH2:39].CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(O)(C)C>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]([NH:39][CH2:38][CH:37]([O:40][CH3:41])[O:36][CH3:35])=[O:33])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 184508304-amino-3-(3-methoxy-4-(1-methyl-1H-indole-2-carboxamido)phenyl)thieno[3,2-c]pyridine-7-carboxylic acid

생성물 1

HCID 184508404-Amino-N-(2,2-dimethoxyethyl)-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridine-7-carboxamide수율 71%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

4-amino-3-(3-methoxy-4-{[(1-methyl-1H-indol-2-yl)carbonyl]amino}phenyl)thieno[3,2-c]pyridine-7-carboxylic acid (1.0 g, 2.1 mmol) and 2,2-dimethoxy-1-ethanamine (252 uL, 2.3 mmol) were reacted according to General Procedure D. MP-carbonate resin (5 g) was added, and the mixture was shaken for 2 hours. The resin was filtered from the mixture and the filtrate was concentrated in vacuo to yield 1.5 g crude material. Isopropyl alcohol (35 mL) was added and the crude product was triturated and filtered to yield the title compound (830 mg, 71% yield): 1H NMR (DMSO, 400 MHz) δ 9.48 (s, 1H), 8.56 (s, 2H), 7.98 (d, 1H), 7.69 (d, 1H), 7.56-7.58 (m, 2H), 7.31-7.33 (m, 2H), 7.04-7.17 (m, 3H), 4.54 (t, 1H), 4.02 (s, 3H), 3.89 (s, 3H), 3.37 (t, 2H), 3.31 (s, 6H), 2.51 (t, 2H); RP-HPLC (Conditions j) Rt 12.2 min. MS: 560.0 MH+.

후처리

  1. filtrationThe resin was filtered from the mixture
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto yield 1.5 g crude material
  4. customthe crude product was triturated
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-48bd387e69e544afa47b3d3f5b1b5535
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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