2-(3-Carbamoylphenylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acid → 3-((R)-2-((R)-2-(5-(3,3-Dimethylureido)-2-(isopropylsulfonyl)phenyl)pyrrolidin-1-yl)-1-(4-fluoro-3-methoxyphenyl)-2-oxoethylamino)benzamide

HRID 1515534Notes

Reaction equation

HRID 1515534 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[NH2:2].Cl.[CH:25]([S:28]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:42])[N:39]([CH3:41])[CH3:40])=[CH:33][C:32]=1[C@H:43]1[CH2:47][CH2:46][CH2:45][NH:44]1)(=[O:30])=[O:29])([CH3:27])[CH3:26]>>[CH3:41][N:39]([CH3:40])[C:38](=[O:42])[NH:37][C:34]1[CH:35]=[CH:36][C:31]([S:28]([CH:25]([CH3:26])[CH3:27])(=[O:30])=[O:29])=[C:32]([C@H:43]2[CH2:47][CH2:46][CH2:45][N:44]2[C:12](=[O:14])[C@H:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:1]([NH2:2])=[O:3])[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH:33]=1

Participants

3

Reactant 2

HCID 594794112-(3-Carbamoylphenylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acidHCID 68439178(R)-3-(4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)-1,1-dimethylurea hydrochloride

Product 1

HCID 594794673-((R)-2-((R)-2-(5-(3,3-Dimethylureido)-2-(isopropylsulfonyl)phenyl)pyrrolidin-1-yl)-1-(4-fluoro-3-methoxyphenyl)-2-oxoethylamino)benzamide

Procedure

Example 59 was prepared according to the general coupling condition using 7D and 31A. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.15 (d, J=6.57 Hz, 3 H) 1.40 (d, J=6.82 Hz, 3H) 1.64-1.80 (m, 1H) 1.92-2.20 (m, 2H) 2.39-2.57 (m, 1H) 2.97 (s, 6H) 3.62-3.76 (m, 4H) 3.81-3.95 (m, 1H) 4.06-4.18 (m, 1H) 5.38 (s, 1H) 5.63 (dd, J=8.08, 5.05 Hz, 1H) 6.78-6.89 (m, 2H) 6.93-7.08 (m, 3H) 7.09-7.22 (m, 3H) 7.25 (dd, J=8.72, 2.15 Hz, 1H) 7.69 (d, J=8.84 Hz, 1H), LC-MS 640 (M+H).

Workup

  1. customExample 59 was prepared

Sources & evidence

ORD record
ord-dc5f919613ae40fd8374c8ebf1d02e85
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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