Sodium Carbonate → N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1H-indole-2-carboxamide

HRID 2257131ノート

反応式

HRID 2257131 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[O:19][CH3:20])[N:6]=1.C([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[C:33](O)=[O:34])(=O)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CO.O.C(N(CC)CC)C>[F:18][C:15]([F:16])([F:17])[C:10]1[CH:11]=[C:12]([O:13][CH3:14])[C:7]([C:5]2[N:6]=[C:2]([NH:1][C:33]([C:25]3[NH:24][C:32]4[C:27]([CH:26]=3)=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:34])[S:3][CH:4]=2)=[C:8]([O:19][CH3:20])[CH:9]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 102198671-acetylindole-2-carboxylic AcidHCID 190280212-Amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole

生成物 1

HCID 19028003N-[4-(4-Trifluoromethyl-2,6-dimethoxyphenyl)-2-thiazolyl]-1H-indole-2-carboxamide収率 60.3%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 0.609 g of 2-amino-4-(4-trifluoromethyl-2,6-dimethoxyphenyl)thiazole, 0.447 g of N-acetyl-2-indolecarboxylic acid, 1.062 g of BOP and 0.243 g of triethylamine in 30 ml of DCM is stirred at r.t. for 48 hours. 100 ml of water are added, and the organic phase is separated after settling has taken place, dried over sodium sulphate and evaporated under vacuum. The derivative acetylated on the indole nitrogen which is obtained is taken up in 50 ml of MeOH, 2 g of sodium carbonate are added and the mixture is stirred overnight at r.t. It is evaporated under vacuum, the residue is taken up with 100 ml of water, the mixture is extracted with DCM, and the organic phase is dried over sodium sulphate and evaporated under vacuum. 0.54 g of the expected product is obtained after crystallization in DCM, m.p.>260° C.

後処理

  1. customthe organic phase is separated after settling
  2. dry with materialdried over sodium sulphate
  3. customevaporated under vacuum
  4. customis obtained
  5. stirringthe mixture is stirred overnight at r.t
  6. customIt is evaporated under vacuum
  7. extractionthe mixture is extracted with DCM
  8. dry with materialthe organic phase is dried over sodium sulphate
  9. customevaporated under vacuum

出典と根拠

ORDレコード
ord-ce4974ec3f6c46f3a515a926a96f07d3
出典データセット
uspto-grants-1997_08
特許番号
US05656648

反応ノート

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