[(4-Fluorobenzyl)sulfonyl]acetic acid → HCID 131727212, compound

HRID 2374056Notes

Reaction equation

[ClH:1].Cl.[NH2:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[C:6]([F:18])[CH:5]=1.[F:19][C:20]1[CH:33]=[CH:32][C:23]([CH2:24][S:25]([CH2:28][C:29](O)=[O:30])(=[O:27])=[O:26])=[CH:22][CH:21]=1>>[ClH:1].[F:19][C:20]1[CH:33]=[CH:32][C:23]([CH2:24][S:25]([CH2:28][C:29]([NH:3][C:4]2[CH:17]=[CH:16][C:7]([O:8][C:9]3[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=3)=[C:6]([F:18])[CH:5]=2)=[O:30])(=[O:26])=[O:27])=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 11447598[(4-Fluorobenzyl)sulfonyl]acetic acid

HCID 60209271HCID 60209271, compound

Product 1

HCID 131727212HCID 131727212, compoundYield 45.6%

Procedure

4-(4-Amino-2-fluorophenoxy)pyridin-2-amine dihydrochloride (50 mg, 0.17 mmol) was coupled with 2-(4-fluorobenzylsulfonyl)acetic acid (33 mg, 0.14 mmol) in a manner similar to that which is described in Step C of Example 1 to give 2-(4-fluorobenzylsulfonyl)-N-(4-(2-aminopyridin-4-yloxy)-3-fluorophenyl)acetamide, hydrochloride salt (30 mg, 45% yield). 1H NMR (DMSO-d6) δ 13.40 (s, 1H), 11.15 (s, 1H), 7.97 (d, 1H, J=7.0 Hz), 7.80-7.90 (m, 3H), 7.47 (m, 4H), 7.26 (t, 2H, J=8.5 Hz), 6.72 (d, 1H, J=7.0 Hz), 6.14 (d, 1H, J=2.0 Hz), 4.69 (s, 2H), 4.27 (s, 2H); MS(ESI+): m/z 434.15 (M+H)+.

Sources & evidence

ORD record: ord-45e1c85ad140454587b7b672f142066b
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459562B2

Reaction notes

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