Diisopropylethylamine → HCID 178480912, compound

HRID 1695649Notes

Reaction equation

HRID 1695649 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH:43]1([NH:50][C:51]2[O:52][CH2:53][C:54]3[CH:60]=[C:59]([NH2:61])[CH:58]=[CH:57][C:55]=3[N:56]=2)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>ClCCl.CN(C)C=O.O>[CH:43]1([NH:50][C:51]2[O:52][CH2:53][C:54]3[CH:60]=[C:59]([NH:61][C:9](=[O:11])[CH2:8][N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)[CH:58]=[CH:57][C:55]=3[N:56]=2)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2762732(4-Methylpiperazin-1-yl)acetic acidHCID 178507250HCID 178507250, compound

Product 1

HCID 178480912HCID 178480912, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(4-Methyl-piperazin-1-yl)-acetic acid (167 mg, 1.1 mmol), N,N-diisopropyl ethyl amine (398 mg, 3.1 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (452 mg, 1.4 mmol) were dissolved in dichloromethane 25 mL) and dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 30 minutes. N2-Cycloheptyl-4H-benzo[d][1,3]oxazine-2,6-diamine (228 mg, 0.88 mmol) was added and stirring was continued overnight. The reaction mixture was diluted with water and thrice extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The crude product was purified by column chromatography (silica gel, dichloromethane/methanol/ammonia 100:0:0−>110:10:1). The title compound (144 mg, 41%) was obtained as an off-white foam; MS: m/e=400.5 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by column chromatography (silica gel, dichloromethane/methanol/ammonia 100:0:0−>110:10:1)

Sources & evidence

ORD record
ord-81c4f6eb004a4ca7bb90291e02352c8e
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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