Methyl 4-bromobenzoate → HCID 57813961, compound

HRID 564369Notes

Reaction equation

HRID 564369 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:33]=[CH:32][C:27](C(OC)=O)=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7].BrC1C=CC([C:44](OC)=[O:45])=CC=1>>[CH3:44][O:45][C:25]1[CH:26]=[CH:27][CH:32]=[CH:33][C:24]=1[N:21]1[CH2:20][CH2:19][CH:18]([N:15]2[CH2:16][CH2:17][C@@H:13]([NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[C:5]3[CH:34]=[CH:35][CH:36]=[C:3]([C:2]([F:37])([F:38])[F:1])[CH:4]=3)[CH2:14]2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 57814018HCID 57814018, compound

Product 1

HCID 57813961HCID 57813961, compound

Procedure

The title compound was synthesized in similar fashion to methyl 4-(4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}piperidin-1-yl)benzoate, substituting bromo-2-methoxybenzene for methyl 4-bromobenzoate, and was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.50-2.20 (m, 5H), 2.25-2.40 (m, 1H), 2.50-2.70 (m, 3H), 2.82 (dd, J=11.1, 6.9 Hz, 1H), 3.13-3.20 (m, 1H), 3.30-3.40 (m, 1H), 3.49-3.51 (m, 2H), 3.84 (s, 3H), 4.00-4.21 (m, 2H), 4.60-4.71 (m, 1H), 6.81-6.90 (m, 2H), 6.93-7.02 (m, 1H), 7.10-7.28 (m, 4H), 7.56 (t, J=8.1 Hz, 1H), 7.73 (d, J=8.1 Hz, 1H), 8.06 (d, J=7.8 Hz, 1H), 8.25 (s, 1H). MS m/z: 505 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-3a218c2668da40d887d2c4e12e54a677
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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