4-Amino-1-methylpiperidine → 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methyl-N-(1-methylpiperidin-4-yl)benzamide

HRID 1880850ノート

反応式

HRID 1880850 の反応式
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=4[CH3:31])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][N:57]1[CH2:62][CH2:61][CH:60]([NH2:63])[CH2:59][CH2:58]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:63][CH:60]5[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]5)=[O:28])=[CH:24][C:23]=4[CH3:31])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

4

反応物 3

HCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580150324-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methyl-benzoic acid

生成物 1

HCID 252535284-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methyl-N-(1-methylpiperidin-4-yl)benzamide

実験手順

The title compound was synthesized from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methylbenzoic acid as described in the General procedure for amide bond synthesis using HATU and 1-methylpiperidin-4-amine. The final compound was purified by reverse phase HPLC and basified to give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42-2.04 (m, 16 H) 2.10-2.22 (m, 3 H) 2.29 (s, 3 H) 2.77 (d, J=11.1 Hz, 2 H) 3.72 (dd, J=7.3, 4.0 Hz, 1 H) 3.98 (t, J=14.0 Hz, 2 H) 4.60 (t, J=8.2 Hz, 1 H) 7.64 (d, J=8.3 Hz, 1 H) 7.68-7.80 (m, 2 H) 8.08 (d, J=7.8 Hz, 1 H) 8.19 (s, 1 H) 8.60 (s, 1 H). [M+H] calc'd for C27H35F2N7O2, 528; found 528.

後処理

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.42-2.04 (m, 16 H) 2.10-2.22 (m, 3 H) 2.29 (s, 3 H) 2.77 (d, J=11.1 Hz, 2 H) 3.72 (dd, J=7.3, 4.0 Hz, 1 H) 3.98 (t, J=14.0 Hz, 2 H) 4.60 (t, J=8.2 Hz, 1 H) 7.64 (d, J=8.3 Hz, 1 H) 7.68-7.80 (m, 2 H) 8.08 (d, J=7.8 Hz, 1 H) 8.19 (s, 1 H) 8.60 (s, 1 H)

出典と根拠

ORDレコード
ord-8c8bf40debe4446eb957f8d61983fe54
出典データセット
uspto-grants-2012_11
特許番号
US08318727B2

反応ノート

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