Trifluoroacetic acid → HCID 57991938、化合物

HRID 2075336ノート

反応式

HRID 2075336 の反応式
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]3[S:15][C:14]([NH:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[N:13][N:12]=3)=[CH:10][C:3]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[CH:21]=1)[CH2:17][NH:16][C:14]1[S:15][C:11]([C:9]2[S:8][C:4]3=[CH:5][N:6]=[CH:7][C:2]([Cl:1])=[C:3]3[CH:10]=2)=[N:12][N:13]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86636673HCID 86636673、化合物

生成物 1

HCID 57991938HCID 57991938、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-Butyl (S)-1-(5-(4-chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-ylamino)-3-(3-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.070 g, 0.12 mmol) was treated with 1 mL TFA in 1 mL DCM for 30 minutes. After removing the solvent, the residue was mixed with 10 mL 2M ammonia in MeOH. The solvent was removed again and the remaining residue was subjected to a silica gel flash chromatography separation using 3.5% 2M ammonia MeOH solution in DCM as the eluant. An-off white solid was obtained as the pure product (0.03 g, y=52%). LCMS (API-ES) m/z (%): 470.1 (100%, M++H); 1H NMR (300 MHz, CDCL3) δ ppm 1.48-1.82 (b, 3H) 2.72 (dd, J=13.56, 8.48 Hz, 1H) 3.00 (dd, J=13.66, 4.99 Hz, 1H) 3.26-3.35 (m, 1H) 3.40-3.50 (m, 1H) 3.61 (dd, J=12.72, 3.67 Hz, 1H) 7.41-7.56 (m, 6H) 8.46 (s, 1H) 8.95 (s, 1H).

後処理

  1. customAfter removing the solvent
  2. additionthe residue was mixed with 10 mL 2M ammonia in MeOH
  3. customThe solvent was removed again
  4. customthe remaining residue was subjected to a silica gel flash chromatography separation
  5. customAn-off white solid was obtained as the pure product (0.03 g, y=52%)

出典と根拠

ORDレコード
ord-b710a2858cf74f9aa1f9f996ba0051d6
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

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