1-Cyclopropyl-5-methoxyisoquinoline-7-carboxylic acid → HCID 16042869, compound

HRID 545188Notes

Reaction equation

HRID 545188 reaction equation
Cl.Cl.[O:3]=[C:4]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[C:23]([CH:27]=3)[C:24]([NH2:26])=[O:25])[CH:17]=2)[O:12][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5]1.[CH:28]1([C:31]2[N:32]=[CH:33][CH:34]=[C:35]3[C:40]=2[N:39]=[C:38]([C:41](O)=[O:42])[CH:37]=[C:36]3[O:44][CH2:45][CH2:46][OH:47])[CH2:30][CH2:29]1.C1(C2C3C(=C(OC)C=C(C(O)=O)C=3)C=CN=2)CC1>>[CH:28]1([C:31]2[N:32]=[CH:33][CH:34]=[C:35]3[C:40]=2[N:39]=[C:38]([C:41]([N:9]2[CH2:10][CH2:11][C:6]4([CH2:5][C:4](=[O:3])[C:18]5[C:13](=[CH:14][CH:15]=[C:16]([C:19]6[CH:20]=[N:21][CH:22]=[C:23]([CH:27]=6)[C:24]([NH2:26])=[O:25])[CH:17]=5)[O:12]4)[CH2:7][CH2:8]2)=[O:42])[CH:37]=[C:36]3[O:44][CH2:45][CH2:46][OH:47])[CH2:29][CH2:30]1

Participants

4

Reactant 3

HCID 574408921-Cyclopropyl-5-methoxyisoquinoline-7-carboxylic acidHCID 667820395-{4-Oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinamide dihydrochlorideHCID 671702138-Cyclopropyl-4-(2-hydroxyethoxy)-1,7-naphthyridine-2-carboxylic acid

Product 1

HCID 16042869HCID 16042869, compound

Procedure

The intended compound was produced according to the procedure described in reference Example 37 but using 5-{4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinamide di-hydrochloride and 8-cyclopropyl-4-(2-hydroxy-ethoxy)-[1,7]naphthyridine-2-carboxylic acid in place of methyl 5-{4-oxospiro[chroman-2,4′-piperidin]-6-yl}nicotinate di-hydrochloride and 1-cyclopropyl-5-methoxyisoquinoline-7-carboxylic acid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.99 (2.0H, dd, J=10.6, 2.1 Hz), 8.48-8.45 (1.0H, m), 8.42 (1.0H, d, J=5.6 Hz), 8.28 (1.0H, br s), 8.11 (1.0H, d, J=2.4 Hz), 8.06 (1.0H, dd, J=8.5, 2.4 Hz), 7.81 (1.0H, d, J=5.6 Hz), 7.64 (1.0H, br s), 7.38 (1.0H, s), 7.29 (1.0H, d, J=8.5 Hz), 5.06 (1.0H, t, J=5.6 Hz), 4.39-4.30 (3.0H, m), 3.90-3.81 (2.0H, m), 3.80-3.70 (1.0H, m), 3.58-3.39 (2.0H, m), 3.37-3.27 (1.0H, m), 2.98 (2.0H, s), 2.17-2.06 (1.0H, m), 2.02-1.80 (3.0H, m), 1.19-1.02 (4.0H, m). MS [M+H]+=594.

Workup

  1. customThe intended compound was produced

Sources & evidence

ORD record
ord-04067056cd444b149eeb6248e4eae299
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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