Isopropylamine → HCID 42641986, 화합물

HRID 2112151노트

반응식

HRID 2112151 반응식
CS(OS(C)(=O)=O)(=O)=O.[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH2:42][CH2:43]O)[N:36]=[CH:35]3)=O)[N:17]([CH3:19])[N:18]=1)([CH3:13])([CH3:12])[CH3:11].[CH:45]([N:48](C(C)C)CC)([CH3:47])[CH3:46].C(N)(C)C.CC#N.[OH2:61]>>[C:10]([C:14]1[CH:15]=[C:16]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH2:42][CH2:43][NH:48][CH:45]([CH3:47])[CH3:46])[N:36]=[CH:35]3)=[O:61])[N:17]([CH3:19])[N:18]=1)([CH3:13])([CH3:12])[CH3:11]

참가 물질

6

반응물 5

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 18373917Acetonitrile--water (1/1)HCID 67409607HCID 67409607, 화합물

생성물 1

HCID 42641986HCID 42641986, 화합물수율 20%

실험 절차

Methanesulfonic anhydride (18 mg, 0.11 mmol) was added to a solution of alcohol (7s) (36 mg, 0.076 mmol) and diisopropylethylamine (29 mg, 0.23 mmol) at room temperature. The solution was stirred for 1 hour. Isopropylamine (0.13 mL, 1.50 mmol) was added and the reaction was stirred at room temperature for 60 hours. The volatiles were removed in vacuo. The crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N and then on C18 silica with CH3CN/H2O to afford the desired compound (8s-2) (8 mg, 20% yield). 1H NMR (400 MHz, MeOD) δ 7.88 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.31-7.24 (m, 3H), 7.17-7.16 (m, 2H), 6.93-6.89 (m, 1H), 6.05 (s, 1H), 4.52 (t, J=10.2 Hz, 2H), 4.41 (s, 2H), 3.57 (s, 3H), 3.35-3.30 (m, 1H), 3.03 (t, J=11.7 Hz, 2H), 2.29-2.22 (m, 2H), 1.29 (d, J=6.3 Hz, 6H), 1.26 (s, 9H); MS (ESI+) m/z 517 (M+H)+; HPLC (5 to 95%) 2.61 min.

후처리

  1. stirringthe reaction was stirred at room temperature for 60 hours
  2. customThe volatiles were removed in vacuo
  3. customThe crude product was purified on silica gel with 5% MeOH/CH2Cl2 containing 1% Et3N

출처 및 근거

ORD 기록
ord-f490aca1a5004659bf6374773e064d3c
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521447B2

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