Water → HCID 178481761、化合物

HRID 246329ノート

反応式

HRID 246329 の反応式
C(OC(=O)[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[C:32]5[C:27](=[CH:28][C:29]([F:33])=[CH:30][CH:31]=5)[N:26]([CH3:34])[N:25]=4)[N:22]=3)[N:17](COCC[Si](C)(C)C)[CH:16]=2)=[O:14])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.C(N)CN.O>ClCCl.C(OCC)(=O)C>[NH2:7][C@@H:8]1[CH2:9][C@H:10]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[C:32]5[C:27](=[CH:28][C:29]([F:33])=[CH:30][CH:31]=5)[N:26]([CH3:34])[N:25]=4)[N:22]=3)[NH:17][CH:16]=2)=[O:14])[CH2:11]1

参加物

7

反応物 4

HCID 962WaterHCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 178481749HCID 178481749、化合物

生成物 1

HCID 178481761HCID 178481761、化合物収率 96.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a round-bottomed flask, (cis-3-{[2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-cyclobutyl)carbamic acid tert-butyl ester (144 mg, 0.236 mmol) was dissolved in dichloromethane (1.2 ml) and trifluoroacetic acid (0.73 ml, 9.48 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was suspended in dichloromethane (1.2 ml) and ethylenediamine (0.96 ml, 14.2 mmol) was added. The light yellow suspension was stirred at room temperature for 1 h then water and ethyl acetate were added. The suspension was filtered and washed with hot water and ethyl acetate. The product was dried under high vacuum to provide 86 mg (91%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (cis-3-amino-cyclobutyl)-amide as a light yellow powder. MS: (M+H)+=380; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.09 (s, 1H), 8.54 (dd, J=8.7, 5.3 Hz, 1H), 8.41 (s, 1H), 8.28 (d, J=7.6 Hz, 1H), 7.71 (dd, J=9.8, 1.9 Hz, 1H), 7.28 (td, J=9.1, 1.9 Hz, 1H), 5.54 (br. s., 2H), 4.15 (s, 3H), 4.04-4.18 (m, 1H), 3.07-3.22 (m, 1H), 2.65-2.80 (m, 2H), 1.66-1.80 (m, 2H).

後処理

  1. concentrationthen concentrated
  2. stirringThe light yellow suspension was stirred at room temperature for 1 h
  3. filtrationThe suspension was filtered
  4. washwashed with hot water and ethyl acetate
  5. customThe product was dried under high vacuum

出典と根拠

ORDレコード
ord-eebc29b40d604fa5aa47e1d2a08e5659
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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