Ethyl Bromide → HCID 67004649, compound

HRID 564408Notes

Reaction equation

HRID 564408 reaction equation
[CH2:1]([O:3][C@@H:4]1[CH2:8][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6][C@H:5]1[NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[CH3:2].Br[CH:33](C)C.BrCC>>[CH:1]([O:3][C@@H:4]1[CH2:8][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6][C@H:5]1[NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=1)([CH3:33])[CH3:2]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 63582-BromopropaneHCID 67005159HCID 67005159, compound

Product 1

HCID 67004649HCID 67004649, compound

Procedure

The title compound was synthesized in similar fashion to rel-N-(2-{[(3R,4R)-4-ethoxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide, 2-bromopropane was substituted for bromoethane, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.10 (d, J=6.0 Hz, 3H), 1.15 (d, J=6.0 Hz, 3H), 1.40-1.60 (m, 2H), 1.64-1.80 (m, 2H), 2.17-2.26 (m, 1H), 2.20-2.40 (m, 1H), 2.64-2.78 (m, 2H), 3.21-3.43 (m, 3H), 3.75-3.90 (m, 2H), 3.90-4.00 (m, 2H), 4.07-4.17 (m, 2H), 4.18-4.25 (m, 1H), 6.47-6.60 (m, 1H), 7.20-7.30 (m, 1H), 7.56 (t, J=7.5 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.99 (d, J=7.5 Hz, 1H), 8.08 (s, 1H). MS m/z: 458 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-4bcd53fd6e5b44d6a14e07b58e748b67
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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