7-methoxynaphthalene-2-sulfonyl Chloride → HCID 69780337, compound

HRID 2304247Notes

Reaction equation

HRID 2304247 reaction equation
Cl.COC(=O)C(NS(C1C=CC2C(=CC=CC=2)C=1)(=O)=O)CC1C=C2C(=CC=1)C(N)=NC=C2.Cl.Cl.[CH3:35][O:36][C:37](=[O:52])[CH:38]([NH2:51])[CH2:39][C:40]1[CH:49]=[C:48]2[C:43]([CH:44]=[CH:45][N:46]=[C:47]2[NH2:50])=[CH:42][CH:41]=1.[CH3:53][O:54][C:55]1[CH:64]=[C:63]2[C:58]([CH:59]=[CH:60][C:61]([S:65](Cl)(=[O:67])=[O:66])=[CH:62]2)=[CH:57][CH:56]=1>>[CH3:35][O:36][C:37](=[O:52])[CH:38]([NH:51][S:65]([C:61]1[CH:60]=[CH:59][C:58]2[C:63](=[CH:64][C:55]([O:54][CH3:53])=[CH:56][CH:57]=2)[CH:62]=1)(=[O:67])=[O:66])[CH2:39][C:40]1[CH:49]=[C:48]2[C:43]([CH:44]=[CH:45][N:46]=[C:47]2[NH2:50])=[CH:42][CH:41]=1

Participants

4

Reactant 3

HCID 105152667-methoxynaphthalene-2-sulfonyl ChlorideHCID 69780573HCID 69780573, compoundHCID 69781962HCID 69781962, compound

Product 1

HCID 69780337HCID 69780337, compound

Procedure

Using the procedure described for 11a, methyl ester 37i and compound 12a gave 3-(1-amino-7-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 4 to give 37. 1H-NMR 200 MHz (CD3OD) δ: −0.20-0.77 (5H, m), 1.22-1.58 (3H, m), 1.73-3.20 (4H, m), 3.65-4.19 (2H, m), 3,93 (3H, s), 4.53-4.68 (1H, m), 7.00-7.06 (1H, m), 7.23-7.31 (2H, m), 7.43-7.51 (2H, m), 7.56-8.15 (6H, m).

Sources & evidence

ORD record
ord-a2ea75b4bd4a4c71a56a99b8074e60ab
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

Loading…