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Hydrochloric Acid → HCID 178457040、化合物

HRID 2040675
ノート
印刷プレビュー

反応式

HRID 2040675 の反応式
[C:1]([C:5]1[CH:52]=[CH:51][C:8]2[N:9](COCC[Si](C)(C)C)[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([CH2:17][N:18]([CH2:22][C@@H:23]4[C@H:27]5[O:28]C(C)(C)[O:30][C@H:26]5[C@H:25]([N:33]5[C:37]6[N:38]=[CH:39][N:40]=[C:41]([NH2:42])[C:36]=6[CH:35]=[CH:34]5)[CH2:24]4)[CH:19]([CH3:21])[CH3:20])[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CO>[NH2:42][C:41]1[C:36]2[CH:35]=[CH:34][N:33]([C@@H:25]3[CH2:24][C@H:23]([CH2:22][N:18]([CH2:17][CH:15]4[CH2:14][CH:13]([CH2:12][C:10]5[NH:9][C:8]6[CH:51]=[CH:52][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=6[N:11]=5)[CH2:16]4)[CH:19]([CH3:20])[CH3:21])[C@@H:27]([OH:28])[C@H:26]3[OH:30])[C:37]=2[N:38]=[CH:39][N:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 677748577-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

生成物 1

HCID 178457040HCID 178457040、化合物収率 55.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

7-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (58.7 mg, 0.08 mmol) was dissolved in cone. HCl solution (5 ml) and methanol (5 ml) and heated to 40° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml). The layers were separated and the aqueous layer was extracted with EtOAc (2×10 ml), the combined organics were then dried (MgSO4) and concentrated. The crude material was purified by prep TLC, eluting with 10% 2M NH3 in MeOH in DCM to afford the title compound (24.7 mg, 55%) as a colourless gum: MS (ESI+) for C32H45N7O2 m/z 560.4 [M+H]+; LC purity 100% (UV), (ret. time, 5.10 min); 1H NMR (500 MHz, Acetone) δH 8.12 (s, 1 H), 7.30-7.60 (m, 2 H), 7.13-7.28 (m, 2 H), 6.54 (d, J=3.5 Hz, 1 H), 6.33 (br. s., 1 H), 4.85-5.07 (m, 1 H), 4.36 (t, J=6.2 Hz, 1 H), 4.08 (t, J=5.2 Hz, 1 H), 3.01 (d, J=7.7 Hz, 1 H), 2.93 (d, J=7.4 Hz, 2 H), 2.78 (br. s., 2 H), 2.59-2.73 (m, 2 H), 2.15-2.56 (m, 7 H), 1.68 (dt, J=12.4, 9.7 Hz, 1 H), 1.44-1.62 (m, 2 H), 1.35 (s, 9 H), 0.90-1.07 (m, 6 H).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between sat. NaHCO3(aq) (10 ml) and EtOAc (10 ml)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×10 ml)
  5. dry with materialthe combined organics were then dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by prep TLC
  8. washeluting with 10% 2M NH3 in MeOH in DCM

出典と根拠

ORDレコード
ord-d053d428858a4848be5f50ddac97a710
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08580762B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート