Trifluoroacetic acid → (S)-2-Methoxyethyl 1-(5-(2-aminophenylcarbamoyl)pyridin-2-yl)pyrrolidin-3-ylcarbamate

HRID 1661505ノート

反応式

HRID 1661505 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=C[C:14]([N:17]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:30])[O:24][CH2:25][CH2:26]N(C)C)[CH2:18]2)=[CH:13][CH:12]=1)=[O:10].[NH2:31][C@H]1CCN(C2C=CC(C(NC3C=CC=CC=3NC(=O)OC(C)(C)C)=O)=CN=2)C1.[C:60]([OH:66])(C(F)(F)F)=O.Cl.O1CCOCC1>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([N:17]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:30])[O:24][CH2:25][CH2:26][O:66][CH3:60])[CH2:18]2)=[N:31][CH:16]=1)=[O:10]

参加物

5

反応物 4

HCID 6422Trifluoroacetic acidHCID 204431481,4-Dioxane hydrochlorideHCID 59806005(S)-2-(Dimethylamino)ethyl 1-(4-(2-aminophenylcarbamoyl)phenyl)pyrrolidin-3-ylcarbamateHCID 59806014(S)-tert-Butyl 2-(6-(3-aminopyrrolidin-1-yl)nicotinamido)phenylcarbamate

生成物 1

HCID 59806011(S)-2-Methoxyethyl 1-(5-(2-aminophenylcarbamoyl)pyridin-2-yl)pyrrolidin-3-ylcarbamate

実験手順

Following the procedures described above for the synthesis of compound 119 (Scheme 1, Example 1, steps 4 and 5) but replacing compound 117 with the compound 153, and TFA for HCl/dioxane, title compound 154 was obtained as a beige solid. 1H NMR: (DMSO) δ (ppm): 9.42 (s, 1H), 8.72 (d, J=2.3 Hz, 1H), 8.05 (dd, J=8.8, 2.3 Hz, 1H), 7.65 (d, J=6.5 Hz, 1H), 7.13 (d, J=7.8 Hz, 1H), 6.95 (td, J=7.6, 1.4 Hz, 1H), 6.77 (dd, J=8.0, 1.2 Hz, 1H), 6.58 (td, J=7.5, 1.4 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 4.87 (s, 2H), 4.17 (q, J=5.7 Hz, 1H), 4.08 (t, J=4.6 Hz, 2H), 3.67 (q, J=5.7 Hz, 1H), 3.57-3.55 (m, 1H), 3.50-3.47 (m, 3H). 3.3 (m, overlap with water, 1H), 3.25 (s, 3H), 2.22-2.14 (m, 1H), 1.96-1.88 (m, 1H). LRMS (ESI): (calc.) 399.2; (obt.) 400.3 (M+H)+.

出典と根拠

ORDレコード
ord-62abfc28d8cb4db78e3752c329b8be03
出典データセット
uspto-grants-2011_10
特許番号
US08030344B2

反応ノート

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