Phosgene → HCID 59199336、化合物

HRID 2089545

反応式

HRID 2089545 の反応式
[N+](C1NC=NC=1)([O-])=O.[N+:9]([C:12]1[N:16]([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)[CH:15]=[N:14][CH:13]=1)([O-])=O.[C:27](Cl)(Cl)=[O:28].[CH:31]1([NH2:34])[CH2:33][CH2:32]1>[Pd]>[CH:31]1([NH:34][C:27]([NH:9][C:12]2[N:16]([CH:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)[CH:15]=[N:14][CH:13]=2)=[O:28])[CH2:33][CH2:32]1

参加物

6

反応物 4

HCID 6371PhosgeneHCID 182084-NitroimidazoleHCID 69828CyclopropylamineHCID 59199381HCID 59199381、化合物

生成物 1

HCID 59199336HCID 59199336、化合物

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

In the first step a modified Mitsunobu reaction employing 5-nitro-1H-imidazole (CAS #3034-38-6) can be preformed as described in Example 1. The resulting 5-nitro-1(1,2,3,4-tetrahydro-naphthalen-1-yl)-1H-imidazole, can then be reduced via the employment of palladium on carbon under a hydrogen atmosphere. The resulting amine can undergo treatment with phosgene followed by the addition of cyclopropylamine to afford 1-cyclopropyl-3-[3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazol-4-yl]-urea; MS: (ESI) m/z 297.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.46-0.57 (m, 2 H), 0.68-0.77 (m, 2 H), 1.78-2.29 (m, 4 H), 2.49-2.60 (m, 1 H), 2.79-3.01 (m, 2 H), 5.17-5.31 (m, 1 H), 5.34-5.43 (m, 1 H), 6.33-6.43 (m, 1 H), 6.85 (d, J=7.6 Hz, 1 H), 7.01 (s, 1 H), 7.13 (t, J=7.5 Hz, 1 H), 7.17-7.26 (m, 3 H).

後処理

  1. customIn the first step a modified Mitsunobu reaction

出典と根拠

ORDレコード
ord-2ee919f6629f41c885d0e1a98e54f52e
出典データセット
uspto-grants-2013_05
特許番号
US08436035B2

関連ノート

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