Diisopropylethylamine → HCID 24772470, compound

HRID 1015589Notes

Reaction equation

HRID 1015589 reaction equation
[CH3:1][CH:2]1[O:6][CH2:5][C:4]2[S:7][C:8]([NH:13][C:14]([C:16]34[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]5)[O:17]3)[CH2:23]4)=[O:15])=[C:9]([C:10](O)=[O:11])[C:3]1=2.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[F:60][C:61]1([F:65])[CH2:64][NH:63][CH2:62]1>CN(C)C=O.C(OCC)(=O)C>[F:60][C:61]1([F:65])[CH2:64][N:63]([C:10]([C:9]2[C:3]3[CH:2]([CH3:1])[O:6][CH2:5][C:4]=3[S:7][C:8]=2[NH:13][C:14]([C:16]23[CH2:25][CH:20]4[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]4)[O:17]2)[CH2:23]3)=[O:15])=[O:11])[CH2:62]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 67300629HCID 67300629, compound

Product 1

HCID 24772470HCID 24772470, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from example 43A (90 mg, 0.25 mmol) in N,N-dimethylformamide (0.5 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol), N,N diisopropylethylamine (0.3 mL, 1.7 mmol), and 3,3-difluoroazetidine hydrochloride (130 mg, 1 mmol). The mixture was stirred at room temperature for 18 hours, diluted with ethyl acetate (10 mL) and washed with water and brine. The organic extract was dried over MgSO4 and concentrated. Purification by chromatography (0 to 75% ethyl acetate in hexane gradient) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.28 (d, J=6.4 Hz, 3H) 1.63-2.06 (m, 11H) 2.18 (s, 2H) 4.35-4.71 (m, 4H) 4.81-5.00 (m, 2H) 5.29-5.42 (m, 1H) 11.12 (s, 1H). MS (DCI/NH3) m/z 439.1 (M+H)+.

Workup

  1. washwashed with water and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated
  5. customPurification by chromatography (0 to 75% ethyl acetate in hexane gradient)

Sources & evidence

ORD record
ord-adcd9df641a84bbd9168034e53403347
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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