Ro3280 → 4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

反応式

[CH:1]1([N:6]2[CH2:12][C:11](F)([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:37]=[CH:36][C:25]([C:26]([NH:28][CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:38][CH3:39])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.NCC(F)([C:46]([F:49])([F:48])[F:47])C(O)=O>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([C:46]([F:49])([F:48])[F:47])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:37]=[CH:36][C:25]([C:26]([NH:28][CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:38][CH3:39])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

反応物 2

HCID 25015677Ro3280

HCID 866358942-(Aminomethyl)tetrafluoropropanoic acid

生成物 1

HCID 252527644-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-7-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

実験手順

The title compound was synthesized using the analogous procedure to that described in connection with Compound 3 except that 2-(aminomethyl)-2,3,3,3-tetrafluoropropanoic acid was used as the starting material. The final product was purified on reversed phase HPLC as TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46-1.76 (m, 10H) 1.83-2.09 (m, 4H) 2.19 (s, 3H) 2.80 (d, J=11.9 Hz, 2H) 3.32 (s, 3H) 3.69-3.81 (m, 1H) 3.89 (t, 1H) 3.94 (s, 3H) 4.15-4.35 (q, 1H) 4.72 (quin., J=8.1 Hz, 1H) 7.48 (dd, J=1.77 Hz, 1H) 7.50 (s, 1H) 8.00 (s, 1H) 8.10 (d, J=7.8 Hz, 1H) 8.26 (d, J=8.3 Hz, 1H) 8.32 (s, 1H). [M+H] calc'd for C28H35F4N7O3 594. found 594.

後処理

customThe final product was purified on reversed phase HPLC as TFA salt

出典と根拠

ORDレコード: ord-38954b45c33b42bf9970e6cc162a1be0
出典データセット: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08026234B2

反応ノート

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