Trifluoroacetic acid → HCID 71626045、化合物

HRID 1396460ノート

反応式

HRID 1396460 の反応式
[C:1]([C:4]1[N:9]=[N:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([C:35]#[N:36])([CH3:34])[CH3:33])[N:27]=1)(=[O:3])[NH2:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:7]1[N:8]=[N:9][C:4]([C:1]([NH2:2])=[O:3])=[C:5]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([C:35]#[N:36])([CH3:34])[CH3:33])[N:27]=2)[CH:6]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86689795HCID 86689795、化合物

生成物 1

HCID 71626045HCID 71626045、化合物収率 57.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl (1S,2R)-2-(6-carbamoyl-5-(6-(2-cyanopropan-2-yl)pyridin-2-ylamino)pyridazin-3-ylamino)cyclohexylcarbamate (110 mg, 222 μmol) in CH2Cl2 (3.00 mL) was added TFA (1.48 g, 1.00 mL, 13.0 mmol) and the reaction mixture stirred to room temperature for 18 h. Solvents evaporated and residue purified by flash column (spherical silica 20-45 μM, 23 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2 to give 6-((1R,2S)-2-aminocyclohexylamino)-4-(6-(2-cyanopropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxamide (50 mg, 57% yield) as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 11.47 (s, 1H), 8.76 (s, 1H), 8.06 (d, J=3.0 Hz, 1H), 7.60 (t, J=7.9 Hz, 1H), 6.86 (d, J=7.6 Hz, 1H), 6.78 (d, J=7.9 Hz, 1H), 5.60-5.77 (m, 2H), 4.25 (br. s., 1H), 3.11-3.24 (m, 1H), 1.32-1.92 (m, 16H); LC-MS 395.1 [M+H]+.

後処理

  1. customSolvents evaporated
  2. customresidue purified by flash column (spherical silica 20-45 μM, 23 g, Versaflash Supelco)
  3. washeluting with 0 to 5% over 20 min (MeOH containing 10% NH4OH)/CH2Cl2

出典と根拠

ORDレコード
ord-4f2563316ef741d489239db8f278cb36
出典データセット
uspto-grants-2014_12
特許番号
US08901124B2

反応ノート

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