Diisopropylethylamine → HCID 66920661, compound

HRID 1364558Notes

Reaction equation

HRID 1364558 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:27]=[CH:26][C:20]([O:21][CH2:22][C:23](O)=[O:24])=[CH:19][CH:18]=2)=[O:14])[CH:3]=1.Cl.CN.F[B-](F)(F)F.[N:36]1(OC(N(C)C)=[N+](C)C)[C:40]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(#N)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]([O:21][CH2:22][C:23]([NH:36][CH3:40])=[O:24])=[CH:26][CH:27]=2)=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6364545Methylamine hydrochlorideHCID 66920731HCID 66920731, compound

Product 1

HCID 66920661HCID 66920661, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of Example 188B (19 mg, 0.05 mmol), methylamine HCl salt (7 mg, 0.1 mmol) in N,N-dimethylformamide (500 μL) was added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (18 mg, 0.055 mmol), followed by N,N-diisopropylethylamine (44 μL). The reaction mixture was stirred at ambient temperature for 1 hr. It was diluted with 1 mL acetonitrile and purified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to provide the titled compound as white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.95 (t, J=6.4 Hz, 1H), 8.00-7.94 (m, 1H), 7.29 (bs, 2H), 7.23 (d, J=8.9 Hz, 2H), 7.07 (s, 1H), 6.91 (d, J=8.9 Hz, 2H), 4.49 (q, J=7.1 Hz, 2H), 4.42 (s, 2H), 4.40 (d, J=6.4 Hz, 2H), 2.65 (d, J=4.6 Hz, 3H), 1.31 (t, J=7.1 Hz, 3H). MS (m/e) 384 (M+H)+.

Workup

  1. custompurified by reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate)

Sources & evidence

ORD record
ord-0f781721945340a6be19ab6b6ec8aece
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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