Diisopropylethylamine → HCID 58203926, compound

HRID 1849367Notes

Reaction equation

HRID 1849367 reaction equation
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.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.[Br:41][C:42]1[CH:43]=[CH:44][C:45]2[C:51]3[S:52][C:53]([C:55]([N:57]([C:59]4[CH:60]=[C:61]([CH:65]=[CH:66][C:67]=4[Cl:68])[C:62](O)=[O:63])[CH3:58])=[O:56])=[CH:54][C:50]=3[CH2:49][CH2:48][O:47][C:46]=2[CH:69]=1>C1COCC1.O>[Br:41][C:42]1[CH:43]=[CH:44][C:45]2[C:51]3[S:52][C:53]([C:55]([N:57]([C:59]4[CH:60]=[C:61]([C:62]([N:5]5[CH2:6][C:3]([F:7])([F:2])[CH2:4]5)=[O:63])[CH:65]=[CH:66][C:67]=4[Cl:68])[CH3:58])=[O:56])=[CH:54][C:50]=3[CH2:49][CH2:48][O:47][C:46]=2[CH:69]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 568343723-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoic acid

Product 1

HCID 58203926HCID 58203926, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3,3-difluoroazetidine hydrochloride (1.18 g, 9.13 mmol), DIPEA (5 mL), HATU (2.78 g, 7.31 mmol) in THF (60 mL) was added 3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoic acid (3.00 g, 6.09 mmol) under nitrogen atmosphere at room temperature. The reaction mixture was stirred for 5 h, diluted with water, extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated in vacuo to give 8-bromo-N-(2-chloro-5-(3,3-difluoroazetidine-1-carbonyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (3.2 g, yield 93%). 1H NMR (DMSO, 400 MHz): δ7.56-6.59 (m, 7H, ArH), 4.76-4.48 (m, 4H, 2CH2), 4.31 (t, J=5.2 Hz, 2H, CH2), 3.33 (s, 3H, CH3), 2.96 (t, J=5.2 Hz, 2H, CH2)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5579584a0a34c99a4364b3ea48be790
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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