HCID 60206867, compound → HCID 60206866, compound

HRID 1296120Notes

Reaction equation

HRID 1296120 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34]CC1C=CC=CC=1)[CH2:6][C@H:7]([NH:27][C:28](=[O:30])[CH3:29])[C@H:8]([OH:26])[CH2:9][NH:10][C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[CH:18]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>[Pd]>[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[OH:34])[CH2:6][C@H:7]([NH:27][C:28](=[O:30])[CH3:29])[C@H:8]([OH:26])[CH2:9][NH:10][C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[CH:18]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

3

Reactant 1

HCID 60206867HCID 60206867, compound2×

Product 1

HCID 60206866HCID 60206866, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following essentially the procedure of EXAMPLE 71, Step 3, the product from step 2, compound 19, (0.19 g, 0.32 mmol) is deprotected under 20 psi of H2 in the presence of 54 mg of 10% palladium on carbon in 3.5 h, affording, after filtration, concentration and treatment with ethereal HCl, 20 (0.16 g, 0.32 mmol, quant.) as a cream-white solid: 1H NMR (CDCl3+CD3OD drop) δ 7.43–7.27 (m, 4H), 6.86–6.77 (m, 3H), 3.95 (br, 1H), 3.8 (br, 1H), 2.93 (m, 2H), 2.6 (m, 4H), 2.4 (m, 1H), 2.06 (m, 2H), 1.85 (s, 3H), 1.8 (m, 2H), 1.59 (m, 1H), 1.5–1.3 (m, 3H), 1.27 (d, J=7 Hz, 6H); IR (diffuse reflectance) 3251, 3113, 3087, 3061, 3053, 3028, 2956, 2941, 2865, 2810, 1645, 1596, 1520, 1446, 1294 cm−1. MS (CI) m/z (rel intensity) 457 (MH+, 99), 459 (5), 458 (25), 457 (99), 439 (3), 257 (7), 218 (5), 202 (3), 201 (9), 96 (4), 77 (3). HRMS (ESI) calcd for C27H37N2O3F+H1 457.2866, found 457.2855. Anal. Calcd for C27H37FN2O3.HCl.1.5 H2O: C, 62.35; H, 7.95; N, 5.39; Found: C, 62.63; H, 7.76; N, 5.47.

Workup

  1. customaffording
  2. filtrationafter filtration, concentration and treatment with ethereal HCl, 20 (0.16 g, 0.32 mmol, quant.) as a cream-white solid

Sources & evidence

ORD record
ord-9da855e3c1574b0995d7ee154472868c
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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