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Diisopropylethylamine → 6-{1-[4-(Dimethylamino)butanoyl]-1,2,3,6-tetra-hydropyridin-4-yl}-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2375833
ノート
印刷プレビュー

反応式

HRID 2375833 の反応式
Cl.Cl.Cl.[S:4]1[C:8]2[CH:9]=[C:10]([NH:13][C:14]3[C:15]4[CH:22]=[C:21]([C:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=5)[NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.Cl.[CH3:30][N:31]([CH3:38])[CH2:32][CH2:33][CH2:34][C:35](O)=[O:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:30][N:31]([CH3:38])[CH2:32][CH2:33][CH2:34][C:35]([N:26]1[CH2:25][CH:24]=[C:23]([C:21]2[NH:20][C:16]3[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:10]4[CH:11]=[CH:12][C:7]5[N:6]=[CH:5][S:4][C:8]=5[CH:9]=4)[C:15]=3[CH:22]=2)[CH2:28][CH2:27]1)=[O:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 69274170Benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine trihydrochloride

生成物 1

HCID 58709937
6-{1-[4-(Dimethylamino)butanoyl]-1,2,3,6-tetra-hydropyridin-4-yl}-N-1,3-benzothiazol-6-yl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine trihydrochloride (50.0 mg, 0.11 mmol) in DMF (3 mL) was added 4-(dimethylamino)butyric acid hydrochloride (17 mg, 0.13 mmol), TBTU (42 mg, 0.13 mmol) and N,N-diisopropylethylamine (0.11 mL). The reaction mixture was left to stir at rt over the weekend. The crude mixture was concentrated in vacuo and purified via MDP, which afforded the title compound as a tan solid. MS (ES+): m/z: 461.99 (100) [MH+]. HPLC: tr=1.82 min (ZQ2000: polar—5 min). 1H NMR (400 MHz, DMSO-d6): δ=1.63-1.68 (m, 2H), 2.10 (s, 3H), 2.11 (s, 3H), 2.18-2.24 (m, 2H), 2.33-2.43 (m, 2H), 2.54-2.56 (m, 2H), 3.67-3.72 (m, 2H), 4.15 (bs, 1H), 4.21 (bs, 1H), 6.45 (s, 1H), 6.84 (d, J=6.4 Hz, 1H), 7.87 (dd, J=1.6, 8.8 Hz, 1H), 8.03 (d, J=8.8 Hz, 1H), 8.34 (s, 1H), 8.92 (s, 1H), 9.23 (s, 1H), 9.61 (s, 1H), 12.02 (d, J=11.2 Hz, 1H).

後処理

  1. waitThe reaction mixture was left
  2. concentrationThe crude mixture was concentrated in vacuo
  3. custompurified via MDP, which

出典と根拠

ORDレコード
ord-5f955389e0914458b5d01e3df9f07ab7
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07465726B2

反応ノート

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