Isopropylamine → HCID 42641986, compound

HRID 1897441Notes

Reaction equation

HRID 1897441 reaction equation
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]

Participants

6

Reactant 5

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

Product 1

HCID 42641986HCID 42641986, compoundYield 20%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-85a153965fc1415e8231c4e47d1b216b
Source dataset
uspto-grants-2013_08
Patent number
US08518983B2

Reaction notes

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