HCID 21952613、化合物 → HCID 58700364、化合物

反応式

CN1C2C(C(F)(F)F)=CC(NC3C=NC=CC=3)=CC=2C2CNCCC12.[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][C:32]([NH:38]C3C=NC=CC=3C(F)(F)F)=[CH:33][C:34]=2[C:36]#[N:37])[C@@H:29]2[CH2:49][NH:50][CH2:51][CH2:52][C@H:28]12.Br[C:54]1[C:55]([O:61][CH3:62])=[N:56][CH:57]=[C:58]([CH3:60])[CH:59]=1.CC([O-])(C)C.[Na+]>>[CH3:62][O:61][C:55]1[C:54]([NH:38][C:32]2[CH:31]=[C:30]3[C:35](=[C:34]([C:36]#[N:37])[CH:33]=2)[N:27]([CH3:26])[C@H:28]2[CH2:52][CH2:51][NH:50][CH2:49][C@@H:29]32)=[CH:59][C:58]([CH3:60])=[CH:57][N:56]=1

参加物

反応物 4

HCID 21952613HCID 21952613、化合物

HCID 219527573-Bromo-2-methoxy-5-methylpyridine

HCID 23676156Sodium t-butoxide

HCID 58700425(4aS,9bR)-5-methyl-8-(4-trifluoromethyl-pyridin-3-ylamino)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

生成物 1

HCID 58700364HCID 58700364、化合物

実験手順

The title compound was prepared by following the general method for (5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-pyridin-3-yl-amine (Method B) as a tan solid (57 mg, 39%) from (4aS,9bR)-8-amino-6-cyano-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylic acid tert-butyl ester (Example 162, 150 mg, 0.46 mmol), 3-bromo-2-methoxy-5-methylpyridine (84 mg, 0.42 mmol) and NaOt-Bu (66 mg, 0.69 mmol): mp 76–80° C.; 1H NMR (300 MHz, CDCl3) δ 7.38 (m, 1H), 7.07 (d, J=2.2 Hz, 1H), 7.00 (d, J=1.8 Hz, 1H), 6.91 (d, J=1.8 Hz, 1H), 5.79 (br s, 1H), 3.99 (s, 3H), 3.63–3.51 (m, 1H), 3.23–3.00 (m, 4H), 2.98–2.79 (m, 2H), 2.73–2.26 (m, 2H), 2.18 (s, 3H), 1.99–1.81 (m, 2H); ESI MS m/z 350 [C20H23N5O+H]+.

出典と根拠

ORDレコード: ord-c0f3dc9f015d46f19508c07b829ac627
出典データセット: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07109339B2

反応ノート

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