Benzo-1,3-dioxole-5-methylamine → HCID 58168056, compound

HRID 1029295Notes

Reaction equation

HRID 1029295 reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH2:27])=[CH:25][C:20]=2[O:19][CH2:18]1>>[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([CH2:26][NH:27][C:2]3[CH:16]=[CH:15][C:5]4[C:6](=[O:14])[NH:7][C:8]5[C:13]([C:4]=4[CH:3]=3)=[CH:12][CH:11]=[CH:10][N:9]=5)=[CH:25][C:20]=2[O:19][CH2:18]1

Participants

3

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168056HCID 58168056, compoundYield 17%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 456 using 6 (266 mg, 1.15 mmol) and benzo[d]-[1,3]dioxol-5-ylmethanamine (697 mg, 4.61 mmol) to provide 476 (67 mg, 17% yield) as a white powder. LC-MS (M+H=346, obsd.=346). 1H NMR (400 MHz, DMSO-D6) δ 11.49 (s, 1H), 8.58 (d, J=6.6, 1H), 8.42 (dd, J=1.6, 4.7, 1H), 7.98 (d, J=8.7, 1H), 7.37 (d, J=2.1, 1H), 7.26 (dd, J=4.7, 7.9, 1H), 7.17 (t, J=6.1, 1H), 7.00 (d, J=1.5, 1H), 6.91 (m, 2H), 6.88 (d, J=7.9, 1H), 5.97 (s, 2H), 4.40 (d, J=5.9, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-b271b9ba3f904fa2a20366debb78caa1
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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