Diisopropylamine → HCID 66920776, compound

HRID 1364564Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=2)=[O:14])[CH:3]=1.Cl.CN.F[B-](F)(F)F.[N:34]1(OC(N(C)C)=[N+](C)C)[C:38]2C=CC=CC=2N=N1.C(NC(C)C)(C)C>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([NH:34][CH3:38])=[O:23])=[CH:24][CH:25]=2)=[O:14])[CH:3]=1

Participants

Reactant 4

HCID 7912Diisopropylamine

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

HCID 6364545Methylamine hydrochloride

HCID 66920940HCID 66920940, compound

Product 1

HCID 66920776HCID 66920776, compoundYield 45.3%

Procedure

To a mixture of Example 231A (17 mg, 0.05 mmol) and methylamine hydrochloride (4 mg, 0.06 mmol), was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (24 mg, 0.06 mmol), followed by N,N-diisopropylamine (21 μL, 0.12 mmol). The mixture was stirred at room temperature for 20 h. The crude product was purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) yielding 8 mg (45%) of the titled compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.31 (t, J=7.0 Hz, 3H), 2.77 (d, J=4.3 Hz, 3H), 4.47-4.57 (m, 4H), 7.07 (s, 1H), 7.27-7.42 (m, 4H), 7.78 (d, J=8.2 Hz, 2H), 8.33-8.40 (m, 1H), 9.11 (q, J=6.1 Hz, 1H). MS (ESI+) m/e=354 (M+H)+.

Workup

customThe crude product was purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record: ord-a7ef90f3cd214b80a7a684b1f53c4dc5
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888374B2

Reaction notes

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