Methyl 4-bromobenzoate → HCID 57814133, compound

HRID 564381Notes

Reaction equation

HRID 564381 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](C3C=CC(C(OC)=O)=CC=3)[CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7].Br[C:40]1[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=1>>[F:37][C:2]([F:1])([F:38])[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[CH2:19][CH2:20][N:21]([C:42]3[CH:41]=[CH:40][CH:49]=[CH:48][C:43]=3[C:44]([O:46][CH3:47])=[O:45])[CH2:22][CH2:23]2)[CH2:14]1)=[O:11])=[O:7]

Participants

3

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 57814018HCID 57814018, compound

Product 1

HCID 57814133HCID 57814133, 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 methyl 2-bromobenzoate for methyl 4-bromobenzoate, and was isolated as a white solid. 1H-NMR (CD3OD) δ: 1.80-2.01 (m, 3H), 2.25-2.45 (m, 2H); 2.51-3.00 (m, 6H), 3.25-3.41 (m, 2H), 3.31-3.45 (m, 2H), 3.87 (s, 3H), 4.05-4.40 (m, 2H), 4.60-4.75 (m, 1H), 6.98-7.20 (m, 1H), 7.20-7.24 (m, 2H), 7.30-7.42 (m, 2H), 7.50-7.60 (m, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.98-8.10 (m, 1H), 8.16 (s, 1H), 8.18-8.30 (m, 1H). MS m/z: 533 (M+1).

Workup

  1. customwas isolated as a white solid

Sources & evidence

ORD record
ord-b3ec3490095f485cbf33d77539014d1e
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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