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

HRID 246587
ノート
印刷プレビュー

反応式

HRID 246587 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:21]([OH:23])=O)=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Cl.[NH2:25][C:26]1([C:29]#[N:30])[CH2:28][CH2:27]1.CCN=C=NCCCN(C)C.O>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:29]([C:26]1([NH:25][C:21]([C:18]2[C:16]3=[N:17][C:12]([C:6]4[C:5]5[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=5)[N:8]([CH3:11])[N:7]=4)=[CH:13][N:14]=[C:15]3[NH:20][CH:19]=2)=[O:23])[CH2:28][CH2:27]1)#[N:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

生成物 1

HCID 71279996N-(1-cyanocyclopropyl)-2-(6-fluoro-1-methyl-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

A mixture of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (90 mg, 0.29 mmol), 1-aminocyclopropanecarbonitrile hydrochloride (41 mg, 0.348 mmol), EDCI (110 mg, 0.58 mmol) and DMAP (75 mg, 0.58 mmol) in DMF (5 mL) was stirred at room temperature for 16 hours. Then the mixture was poured into water (5 mL) and filtered to give the crude product which was purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm; inject volume: 3 mL/inj, flow rate: 20 mL/min; wavelength: 214 nm and 254 nm; the gradient conditions were: 40% acetonitrile/60% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.) to give N-(1-cyanocyclopropyl)-2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (25 mg, 23%) as a white solid. MS: (M+H)+=376; 1H NMR (300 MHz, DMSO): δ 12.95 (s, 1H), 9.10 (s, 1H), 8.87 (s, 1H), 8.56-8.53 (m, 2H), 6.69 (d, 1H, J=8.7 Hz), 7.26 (t, 1H, J=8.7 Hz), 4.15 (s, 3H), 1.70 (brs, 2H), 1.64 (brs, 2H).

後処理

  1. filtrationfiltered
  2. customto give the crude product which
  3. customwas purified by preparative-HPLC (Gemini 5u C18 150×21.2 mm
  4. wait40% acetonitrile/60% water (0.1% trifluoroacetic acid, v/v) initially, proceeding to 55% acetonitrile/45% water (0.1% trifluoroacetic acid, v/v) in a linear fashion over 9 min.

出典と根拠

ORDレコード
ord-b857f4d05f054a9d9d5cb52e627d5340
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

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