2,1,3-Benzothiadiazole-5-carbaldehyde → 4-[(Benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

HRID 1354210

反応式

HRID 1354210 の反応式
[N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([CH:10]=O)[CH:8]=[CH:9][C:2]=12.[NH2:12][CH:13]1[CH2:18][CH2:17][C:16]([CH2:20][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)([OH:19])[CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.ClC(Cl)C>[N:1]1[S:5][N:4]=[C:3]2[CH:6]=[C:7]([CH2:10][NH:12][CH:13]3[CH2:18][CH2:17][C:16]([CH2:20][CH2:21][C:22]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]=[CH:24][N:23]=4)([OH:19])[CH2:15][CH2:14]3)[CH:8]=[CH:9][C:2]=12

参加物

6

反応物 3

HCID 27762902,1,3-Benzothiadiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 211046374-Amino-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

生成物 1

HCID 586031194-[(Benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

Molecular sieve, type 3A, (1 g) and benzo[1,2,5]thiadiazol-5-carbaldehyde (0.066 g, 0.4 mmol) were added to a solution of 4-amino-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol (0.116 g, 0.38 mmol) in methanol (1 ml) and dichloroethane (3 ml). The reaction mixture was stirred at room temperature for 20 hours and sodium triacetoxyborohydride (0.22 g, 1.04 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then filtered over Hydromatrix (wetted with an NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 1% NH4OH).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. filtrationfiltered over Hydromatrix (
  3. washsubsequently washed with dichloromethane
  4. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 1% NH4OH)

出典と根拠

ORDレコード
ord-56d7be57d61c4bbb8529a05b1d9b9aac
出典データセット
uspto-grants-2007_05
特許番号
US07223776B2

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