Diisopropylethylamine → HCID 44464593, compound

HRID 1881701Notes

Reaction equation

HRID 1881701 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[S:42]([N:45]([CH2:49][CH2:50][O:51][CH2:52][C:53](O)=[O:54])[CH:46]1[CH2:48][CH2:47]1)(=[O:44])=[O:43].[F:56][C:57]1[CH:58]=[C:59]([C:63]2([O:69][CH2:70][CH2:71][N:72]3[CH2:76][CH2:75][CH2:74][CH2:73]3)[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[CH:60]=[CH:61][CH:62]=1>O1CCCC1>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[S:42]([N:45]([CH:46]1[CH2:48][CH2:47]1)[CH2:49][CH2:50][O:51][CH2:52][C:53]([N:66]1[CH2:65][CH2:64][C:63]([C:59]2[CH:60]=[CH:61][CH:62]=[C:57]([F:56])[CH:58]=2)([O:69][CH2:70][CH2:71][N:72]2[CH2:76][CH2:75][CH2:74][CH2:73]2)[CH2:68][CH2:67]1)=[O:54])(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57916232HCID 57916232, compoundHCID 57916235HCID 57916235, compound

Product 1

HCID 44464593HCID 44464593, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

DIPEA (2 eq.) and HATU (1.2 eq.) were added to a solution of tetrahydrofuran and 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetic acid [acid K] (1 eq.) at 0° C. 4-(3-Fluorophenyl)-4-(2-(pyrrolidin-1-yl)ethoxy)piperidine [amine C] (1.2 eq.) was taken up in tetrahydrofuran (2 ml/mmol) and the solution was rendered basic with DIPEA (2 eq.) and added to the reaction mixture at 0° C. The reaction mixture was stirred at 25° C. for 16 h. The mixture was concentrated to dryness on a rotary evaporator, the residue was taken up in methylene chloride and the mixture was washed with water and sat. sodium chloride solution and dried over sodium sulfate. The organic phase was concentrated and the crude product was purified by means of column chromatography (5% methanol in methylene chloride). Yield: 60%. MS, Rt=3.6 min, m/z=622.4 [MH]+

Workup

  1. additionadded to the reaction mixture at 0° C
  2. concentrationThe mixture was concentrated to dryness on a rotary evaporator
  3. washthe mixture was washed with water and sat. sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic phase was concentrated
  6. customthe crude product was purified by means of column chromatography (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-1ec14f126924450088744dc979215677
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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