Diisopropylethylamine → HCID 66558137, compound

HRID 41195Notes

Reaction equation

HRID 41195 reaction equation
CN(C(ON1N=NC2C=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1[CH:27]=[C:28]([N:32]2[CH2:36][CH2:35][CH2:34][C@@H:33]2[C:37]2[CH:38]=[C:39]([C:54]([OH:56])=O)[CH:40]=[C:41]3[C:46]=2[O:45][C:44]([N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:43][C:42]3=[O:53])[CH:29]=[CH:30][CH:31]=1.CCN(C(C)C)C(C)C.Cl.N1CCC1>C(Cl)Cl>[N:15]1([C:54]([C:39]2[CH:40]=[C:41]3[C:46](=[C:37]([C@H:33]4[CH2:34][CH2:35][CH2:36][N:32]4[C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=4)[CH:38]=2)[O:45][C:44]([N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)=[CH:43][C:42]3=[O:53])=[O:56])[CH2:14][CH2:13][CH2:10]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochlorideHCID 866724198-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Product 1

HCID 66558137HCID 66558137, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (368 mg, 0.97 mmol) was added to a stirred solution of 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (212 mg, 0.48 mmol >98% enantiomeric purity, see Example 1.06 for details of preparation) and DIPEA (0.674 mL, 3.87 mmol) dissolved in DCM (1 mL) under nitrogen. The resulting solution was stirred at room temperature for 1 h. Azetidine hydrochloride (271 mg, 2.90 mmol) was added and the mixture was stirred at room temperature for 15 h. The reaction mixture was purified by preparative HPLC. The fractions were evaporated to dryness to afford 6-(azetidine-1-carbonyl)-8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4H-chromen-4-one (28 mg, 12%) as a pale yellow foam.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 h
  2. customThe reaction mixture was purified by preparative HPLC
  3. customThe fractions were evaporated to dryness

Sources & evidence

ORD record
ord-1de61a55386c4208afa61e5b0bc17949
Source dataset
uspto-grants-2013_09
Patent number
US08530470B2

Reaction notes

Loading…