Ethyl piperidine-2-carboxylate → 1-[4-(3-{4-[(Benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoyl]piperidine-2-carboxylic acid

HRID 1370962Notes

Reaction equation

HRID 1370962 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:42]1[CH2:52][CH2:51][CH2:50][CH2:49][CH:43]1[C:44]([O:46]CC)=[O:45]>>[CH2:1]([N:8]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=2)[O:30][CH2:31][CH2:32][CH2:33][C:34]([N:42]2[CH2:52][CH2:51][CH2:50][CH2:49][CH:43]2[C:44]([OH:46])=[O:45])=[O:35])=[CH:40][CH:41]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27517Ethyl piperidine-2-carboxylateHCID 185121684-(3-{4-[(benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoic Acid

Product 1

HCID 185121281-[4-(3-{4-[(Benzyl{2-methyl-3-[(methylsulfonyl)amino]phenyl}amino)methyl]phenoxy}phenoxy)butanoyl]piperidine-2-carboxylic acid

Procedure

The product from Example 116B (57 mg, 0.10 mmole) and ethyl pipecolinate (31 mg, 0.20 mmole) were processed as in Example 279A and B to provide the titled compound. 1H NMR (500 MHz, DMSO-d6) δ12.29-13.30 (br.s, 1 H), 8.95 (s, 1 H), 7.24 (m, 8 H), 7.04 (m, 1 H), 6.95 (m, 4 H), 6.69 (m, 1 H), 6.49 (m, 2 H), 5.07 (d, 1 H), 4.06 (s, 2 H), 4.03 (s, 2 H), 3.94 (m, 2 H), 3.77 (d, 1 H), 3.09 (m, 1 H), 2.91 (s, 3 H), 2.49 (m, 2 H), 2.40 (s, 3 H), 2.12 (m, 1 H), 1.90 (m, 2 H), 1.62 (m, 2 H), 1.49 (m, 1 H), 1.35 (m, 1 H), 1.21 (m, 1 H); MS (APCI+) m/z 685.9 (M+H)+.

Sources & evidence

ORD record
ord-5b4e8e7c23ab4504863d8723c8fa6922
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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