4-methyl-1H-indol-5-amine → HCID 68083641, compound

HRID 1470367Notes

Reaction equation

HRID 1470367 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:10][C:3]=12.[CH3:19][C:20]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[O:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:29][C:28]3[C:20]([CH3:19])=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][CH:23]=[CH:22]4)[CH:8]=2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66780330HCID 66780330, compound

Product 1

HCID 68083641HCID 68083641, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(4-methoxyphenyl)furo[3,2-b]pyridine (30.10 mg; 0.12 mmol; 1.00 eq.) instead of 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine, and 4-methyl-1H-indol-5-ylamine (17.79 mg; 0.12 mmol; 1.05 eq.) instead of 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one, and was obtained as a beige solid (27 mg, 64%). (HPLC (method F): 93%, RT: 4.07 min); 1H NMR (500 MHz, DMSO-d6) δ[ppm] 11.14 (s, 1H), 8.49 (s, 1H), 7.92 (d, J=5.5, 1H), 7.90 (d, J=8.8, 2H), 7.38 (t, J=2.7, 1H), 7.30 (d, J=8.4, 1H), 7.27 (s, 1H), 7.06 (d, J=8.9, 2H), 7.00 (d, J=8.5, 1H), 6.52 (s, 1H), 6.06 (d, J=5.5, 1H), 3.83 (s, 3H), 2.36 (s, 3H); MS (m/z) 370 [M+H]+, RT: 3.9 min.

Sources & evidence

ORD record
ord-c37402c497ba4d2d9403741c6bf5d89b
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…