7-methoxynaphthalene-2-sulfonyl Chloride → HCID 69780705, compound

HRID 636918Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:32])[CH:5]([NH:18][S:19]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)(=[O:21])=[O:20])[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([NH2:17])=[N:12][CH:11]=[CH:10]2.Cl.Cl.[CH3:35][O:36]C(=O)C(N)CC1C=C2C(=CC=1)C(N)=NC=C2.COC1C=C2C(C=CC(S(Cl)(=O)=O)=C2)=CC=1>>[CH3:2][O:3][C:4](=[O:32])[CH:5]([NH:18][S:19]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][C:26]([O:36][CH3:35])=[CH:27][CH:28]=2)[CH:23]=1)(=[O:21])=[O:20])[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([NH2:17])=[N:12][CH:11]=[CH:10]2

Participants

Reactant 3

HCID 105152667-methoxynaphthalene-2-sulfonyl Chloride

HCID 69780590HCID 69780590, compound

HCID 69781962HCID 69781962, compound

Product 1

HCID 69780705HCID 69780705, compound

Procedure

Using the procedure described for 11a, the reaction of methyl ester 1j and sulfonyl chloride 12a gave 3-(1-amino-6-isoquinolinyl)-2-[[(7-methoxy-2-naphthalenyl)sulfonyl)amino]propionic acid methyl ester. This ester was saponified and subsequently coupled with 4-methylpiperidine using the procedure described for the previous example to give the title compound 12b. 1H-NMR 200 MHz (CD3OD) δ: 0.18-0.85 (5H, m), 1.22-1.58 (3H, m), 1.78-3.18 (4H, m), 3.80-4.26 (2H, m), 3.88 (3H, s), 4.57-4.72 (1H, m), 6.97-7.04 (1H, m), 7.20-7.79 (8H, m), 8.01-8.14 (2H, m).

Sources & evidence

ORD record: ord-e2e5d2c032ea42928af0e39ae57a82cc
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194409B1

Reaction notes

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