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

반응식

HRID 1354210 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 63651,1-Dichloroethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-56d7be57d61c4bbb8529a05b1d9b9aac
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223776B2

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