Water → N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246671ノート

反応式

HRID 246671 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:21](O)=[O:22])=[CH:19][NH:20][C:15]3=[N:14][CH:13]=2)=[N:3]1.Cl.[NH2:25][C:26]1([C:29]#[N:30])[CH2:28][CH2:27]1.CCN=C=NCCCN(C)C.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:29]([C:26]1([NH:25][C:21]([C:18]2[C:16]3=[N:17][C:12]([C:4]4[C:5]5[C:10](=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=5)[N:2]([CH3:1])[N:3]=4)=[CH:13][N:14]=[C:15]3[NH:20][CH:19]=2)=[O:22])[CH2:28][CH2:27]1)#[N:30]

参加物

7

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 712798782-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

生成物 1

HCID 71279810N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide収率 23%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred mixture of 2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (80 mg, 0.26 mmol) and 1-aminocyclopropanecarbonitrile hydrochloride (46 mg, 0.39 mmol) in DMF (3 mL) was added EDCI (100 mg, 0.52 mmol) followed by DMAP (63 mg, 0.52 mmol). The mixture was stirred at room temperature for 16 hours. Then the mixture was poured into water (5 mL) and filtered, the solid was washed with DMSO and MeOH then dried to give N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (22 mg, 23%) as a white solid. MS: (M+H)+=372; 1H NMR (300 MHz, DMSO): δ 12.98 (s, 1H), 9.14 (s, 1H), 8.95 (s, 1H), 8.55 (s, 1H), 7.58 (s, 1H), 7.25 (d, 1H, J=8.4 Hz), 4.17 (s, 3H), 2.56 (s, 3H), 1.77 (d, 2H, J=6.0 Hz), 1.48-1.44 (m, 2H).

後処理

  1. filtrationfiltered
  2. washthe solid was washed with DMSO and MeOH
  3. customthen dried

出典と根拠

ORDレコード
ord-27add4af0890419c97833b505fee14cc
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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