Formaldehyde → 2-[1-(2-chlorophenyl)-1-methylethyl]-4-(1-methylpyrrolidin-2-yl)-1-[3'-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole

HRID 1673030ノート

反応式

HRID 1673030 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[N:12]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=3)=[CH:23][CH:22]=2)[CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[N:15]=1)([CH3:10])[CH3:9].CO.C=O.[BH3-][C:42]#N.[Na+]>CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[N:12]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=3)=[CH:23][CH:22]=2)[CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:42])[N:15]=1)([CH3:10])[CH3:9]

参加物

6

反応物 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 441772852-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole

生成物 1

HCID 441774952-[1-(2-chlorophenyl)-1-methylethyl]-4-(1-methylpyrrolidin-2-yl)-1-[3'-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3′-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole and MeOH was added formaldehyde, followed by AcOH. The reaction was stirred for 20 min, NaCNBH3 was added to the reaction mixture and was continued to stir for another 30 min. After a routine aqueous work up, the crude product was purified by prep HPLC to give 2-[1-(2-chlorophenyl)-1-methylethyl]-4-(1-methylpyrrolidin-2-yl)-1-[3′-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole: 1H NMR (CD3OD): δ 1.6 (m, 3H,), 1.8 (s, 1H), 1.9 (s, 3H), 2.2-2.5 (m, 4H), 2.8 (s, 3H), 3.2 (s, 3H), 3.6 (br, 1H), 4.7 (m, 1H), 7.1 (m, 1H), 7.2 (m, 5H), 7.4 (s, 1H), 7.7 (m, 3H), 8.0 (m, 2H), 8.2 (m, 1H); LC/MS M+H 534 (observed).

後処理

  1. stirringto stir for another 30 min
  2. customAfter a routine aqueous work up, the crude product was purified by prep HPLC

出典と根拠

ORDレコード
ord-2f8c73f9d3654a38a5ec416bd99f7f9c
出典データセット
uspto-grants-2011_08
特許番号
US07998995B2

反応ノート

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