Methyl Bromide → HCID 67005337, compound

HRID 564401Notes

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)C.CBr.BrCC>>[CH3:1][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:29])[F:27])[CH:21]=1

Participants

Reactant 3

HCID 6323Methyl Bromide

HCID 6332Ethyl Bromide

HCID 67005159HCID 67005159, compound

Product 1

HCID 67005337HCID 67005337, 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, whereby methyl bromide was substituted for bromoethane, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.42-1.60 (m, 2H), 1.67-1.82 (m, 2H), 2.22-2.41 (m, 2H), 2.61-2.80 (m, 2H), 3.19-3.28 (m, 1H), 3.30-3.40 (m, 2H), 3.39 (s, 3H), 3.64-3.70 (m, 1H), 3.90-4.00 (m, 2H), 4.10-4.18 (m, 2H), 4.26-4.36 (m, 1H), 6.56-6.64 (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: 430 (M+1).

Workup

customwas isolated as a white solid

Sources & evidence

ORD record: ord-11b2e9c737d94d14b2fe4979cb4113e5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067457B2

Reaction notes

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