Diisopropylethylamine → HCID 66588902, compound

HRID 1093146Notes

Reaction equation

HRID 1093146 reaction equation
Cl.C([N:9]([C@@H:13]1[C@@:20]2([CH3:24])[C:21]([CH3:23])([CH3:22])[C@H:17]([CH2:18][CH2:19]2)[CH2:16][N:15]2[C:25](=[O:41])[C:26]([OH:40])=[C:27]([C:29](=[O:39])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[N:28]=[C:14]12)C(=O)O)C1C=CC=CC=1.[CH3:42][N:43]([CH3:49])[C:44](=[O:48])[C:45]([OH:47])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][NH:30][C:29]([C:27]2[N:28]=[C:14]3[C@H:13]([NH:9][C:45](=[O:47])[C:44]([N:43]([CH3:49])[CH3:42])=[O:48])[C@@:20]4([CH3:24])[C:21]([CH3:23])([CH3:22])[C@H:17]([CH2:18][CH2:19]4)[CH2:16][N:15]3[C:25](=[O:41])[C:26]=2[OH:40])=[O:39])=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2760995N,N-Dimethyloxamic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66588908HCID 66588908, compound

Product 1

HCID 66588902HCID 66588902, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl((7S,10R,11R)-2-((4-fluorobenzyl)carbamoyl)-3-hydroxy-10,12,12-trimethyl-4-oxo-6,7,8,9,10,11-hexahydro-4H-7,10-methanopyrimido[1,2-a]azocin-11-yl)carbamate hydrochloride salt (0.0367 g, 0.081 mmol), 2-(dimethylamino)-2-oxoacetic acid (9.53 mg, 0.081 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.031 g, 0.081 mmol) and diisopropyl-ethylamine (0.014 mL, 0.081 mmol) in DMF (3 mL) was stirred at room temperature for 24 h. After this the crude reaction mixture was purified by preparative-HPLC using methanol/water (0.1% trifluoroacetic acid) to afford the title compound (0.0301 g, 0.059 mmol, 72% yield) as a purple solid. 1H NMR (500 MHz, CDCl3) δ: 12.01 (1H, s), 8.76 (1 H, t, J=6.0 Hz), 8.21 (1 H, d, J=9.8 Hz), 7.36-7.41 (2 H, m), 6.99-7.05 (2 H, m), 5.27 (1 H, d, J=9.8 Hz), 5.18 (1 H, dd, J=15.6, 8.9 Hz), 4.50-4.63 (2 H, m), 3.65 (1 H, d, J=15.6 Hz), 3.34 (3 H, s), 2.95 (3 H, s), 2.14 (1 H, t, J=8.2 Hz), 1.83-1.94 (1 H, m), 1.47-1.52 (1 H, m), 1.41 (1 H, dd, J=9.5, 5.2 Hz), 1.36 (3 H, s), 1.06 (1 H, dd, 9.8, 4.6 Hz), 1.03 (3 H, s), 0.97 (3 H, s). LCMS (M+H) calcd for C26H33FN5O5: 514.25; found: 514.29.

Workup

  1. customAfter this the crude reaction mixture
  2. customwas purified

Sources & evidence

ORD record
ord-3b394398a11849d790f0c2a0e2d8fc8b
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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