4-Morpholinecarbonyl chloride → HCID 59375076、化合物

HRID 661947ノート

反応式

HRID 661947 の反応式
[N:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:29]2[C:28]3[C:23](=[CH:24][C:25]([OH:30])=[CH:26][CH:27]=3)[NH:22][C:21]=2[C:20]([C:31]([NH2:33])=[O:32])=[CH:19][CH:18]=1>N1C=CC=CC=1.CCOC(C)=O>[N:1]1([C:7]([O:30][C:25]2[CH:26]=[CH:27][C:28]3[C:29]4[C:21](=[C:20]([C:31](=[O:32])[NH2:33])[CH:19]=[CH:18][C:17]=4[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[F:10])[NH:22][C:23]=3[CH:24]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 848104-Morpholinecarbonyl chloride2 回HCID 59375146HCID 59375146、化合物

生成物 1

HCID 59375076HCID 59375076、化合物収率 31.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added to a solution of 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide (Example 40-1, 18.6 mg, 0.058 mmol) in pyridine (1 mL). After 22 h at rt, additional morpholine-4-carbonyl chloride (11.29 mg, 0.075 mmol) was added. After 15 h, the mixture was diluted with EtOAc (30 mL), washed with water (10 mL) and brine (5 mL), and dried and concentrated. The residue was purified by preparative HPLC to provide 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazol-2-yl morpholine-4-carboxylate as a white solid (7.9 mg, 27%). 1H NMR (400 MHz, chloroform-d) δ 9.94 (1H, br. s.), 7.41-7.65 (3H, m), 7.33 (2H, t, J=8.14 Hz), 7.20 (1H, d, J=8.58 Hz), 6.92-7.15 (4H, m), 6.73 (1H, dd, J=8.58, 1.98 Hz), 3.80 (4H, t, J=4.62 Hz), 3.67-3.76 (2H, m), 3.62 (2H, br. s.). Mass spectrum m/z 434.0 (M+H)+.

後処理

  1. waitAfter 15 h
  2. washwashed with water (10 mL) and brine (5 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-4ccc04174d1b4cf78c974d6a8f41c995
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

反応ノート

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